成人免费xx,国产又黄又湿又刺激不卡网站,成人性视频app菠萝网站,色天天天天

Home Cart Sign in  
Chemical Structure| 452972-11-1 Chemical Structure| 452972-11-1

Structure of 452972-11-1

Chemical Structure| 452972-11-1

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

{[proInfo.proName]}

CAS No.: 452972-11-1

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 452972-11-1 ]

CAS No. :452972-11-1
Formula : C11H15BClNO2
M.W : 239.51
SMILES Code : CC1(C)OB(OC1(C)C)C1=CC=CN=C1Cl
MDL No. :MFCD04039873
InChI Key :XFZFMAUUZHBQSS-UHFFFAOYSA-N
Pubchem ID :12067060

Safety of [ 452972-11-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 452972-11-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 6
Fraction Csp3 0.55
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 65.72
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

31.35 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.8
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.03
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.13
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.94
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.58

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.3
Solubility 0.12 mg/ml ; 0.000501 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.12
Solubility 0.184 mg/ml ; 0.000767 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.25
Solubility 0.0136 mg/ml ; 0.0000566 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.77 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

2.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.91

Application In Synthesis of [ 452972-11-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 452972-11-1 ]

[ 452972-11-1 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 109-09-1 ]
  • [ 76-09-5 ]
  • [ 452972-11-1 ]
  • 2
  • [ 52200-48-3 ]
  • [ 76-09-5 ]
  • [ 452972-11-1 ]
  • 3
  • [ 76-09-5 ]
  • [ 78607-36-0 ]
  • [ 452972-11-1 ]
  • 4
  • [ 452972-11-1 ]
  • o-CN-C6H4-Hal [ No CAS ]
  • 2-(2-chloro-pyridin-3-yl)-benzonitrile [ No CAS ]
  • 5
  • [ 452972-11-1 ]
  • [ 6636-78-8 ]
  • 6
  • [ 106-48-9 ]
  • [ 452972-11-1 ]
  • 2-chloro-3-(4-chlorophenoxy)pyridine [ No CAS ]
  • 7
  • [ 452972-11-1 ]
  • potassium (2-chloropyrid-3-yl)trifluoroborate [ No CAS ]
  • 8
  • [ 133038-74-1 ]
  • [ 452972-11-1 ]
  • [ 1426414-39-2 ]
  • 9
  • [ 76-09-5 ]
  • [ 381248-04-0 ]
  • [ 452972-11-1 ]
  • 10
  • [ 452972-11-1 ]
  • [ 1426414-42-7 ]
  • 11
  • [ 452972-11-1 ]
  • [ 1426414-53-0 ]
  • (S)-2-chloro-3-(1-phenylethyl)pyridine [ No CAS ]
  • 12
  • [ 3034-55-7 ]
  • [ 452972-11-1 ]
  • 2-chloro-3-(thiazol-5-yl)-pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; at 120℃; for 0.25h;Microwave irradiation; Svnthesis 32 2-Chlor -3-thiazol-5-yl-pyridine To a degassed suspension of 5-bromothiazole (3 mmol, 0.5 g) and 2-chloro-3-(4, 4,5,5- tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-pyridine (3 mmol, 0.73 g) in 1 ,4-dioxane (14 mL) water (6 mL) was added potassium carbonate (9 mmol, 1.25 g) and bis(triphenylphenylphospine) palladium (II) dichloride (0.15 mmol, 0.10 g). The mixture was heated in a microwave reactor at 120 C for 15 minutes. The mixture was purified by flash chromatography using a gradient elution of 0-100% ethyl acetate/cyclohexane. The solvent was removed by evaporation under reduced pressure to yield the title compound as a low-melting point colourless solid. Yield: 0.42 g, 72%. LCMS, analytical method 1 , TR= 3.37 mins, 95%, M+H=197. H NMR (300 MHz, CDCIs) delta: 8.92 (1 H, s), 8.42 (1 H, d), 8.15 (1 H, s), 7.85 (1 H, d), 7.35 (1 H, m).
  • 13
  • [ 452972-11-1 ]
  • 3-thiazol-5-yl-2-(2-trifluoromethyl-phenyl)-pyridine [ No CAS ]
  • 14
  • [ 452972-11-1 ]
  • 3-(2-bromo-thiazol-5-yl)-2-(2-trifluoromethyl-phenyl)-pyridine [ No CAS ]
  • 15
  • [ 452972-11-1 ]
  • 5-[2-(2-trifluoromethyl-phenyl)-pyridin-3-yl]-thiazol-2-ylamine [ No CAS ]
  • 16
  • [ 452972-11-1 ]
  • N-{5-[2-(2-trifluoromethyl-phenyl)-pyridin-3-yl]-thiazol-2-yl}-isobutyramide [ No CAS ]
  • 17
  • [ 452972-11-1 ]
  • N-{5-[2-(2-trifluoromethyl-phenyl)-pyridin-3-yl]-thiazol-2-yl}-acetamide [ No CAS ]
  • 18
  • [ 452972-11-1 ]
  • phenyl-{5-[2-(2-trifluoromethyl-phenyl)-pyridin-3-yl]-thiazol-2-yl}-amine [ No CAS ]
  • 19
  • [ 1314095-70-9 ]
  • [ 452972-11-1 ]
  • [5-(2-chloro-pyridin-3-yl)-thiazol-2-yl]-propyl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; at 150℃; for 0.25h;Microwave irradiation; Synthesis 41 [5-(2-Chloro- propyl- To a degassed suspension of (5-bromo-thiazol-2-yl)-propyl-carbamic acid tert-butyl ester (2 mmol, 0.64 g) and 2-chloro-3-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-pyridine (2 mmol, 0.5 g) in 1 ,4-dioxane (10 mL) and water (5 mL) was added potassium carbonate (6 mmol, 0.83 g) and bis(triphenylphenylphospine) palladium (II) dichloride (0.01 mmol, 0.070 g). The mixture was heated in a microwave reactor at 150 C for 15 mins. The solvent was removed by evaporation under reduced pressure. Water was added and the mixture was extracted with dichloromethane. The organic phase was collected, dried over MgS04, filtered and evaporated under reduced pressure to give a gum which was purified by flash chromatography using 2: 1 cyclohexane:ethyl acetate as eluent. Fractions were pooled and evaporated under reduced pressure to give the title compound as a colourless oil which solidified on standing. Yield: 0.3 g, 58%. LCMS, analytical method 2, TR=2.75 mins, 100%, Ml+H=254. H NMR (300 MHz, DMSO-d6): 8.26 (1 H, dd); 8.0 (2H, m); 7.56 (1 H, s); 7.4 (1 H, m); 3.21 (2H, q); 1.56 (2H, m); 0.92 (3H, t).
  • 20
  • [ 651780-02-8 ]
  • [ 452972-11-1 ]
  • 5-(2-chloropyridin-3-yl)-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With tetrakis(triphenylphosphine) palladium(0); water; sodium carbonate; In 1,4-dioxane; at 100℃; for 18h;Inert atmosphere; [0150j A single necked round bottom flask (250 mL) equipped with a magnetic stir bar was charged with tert-butyl 5-bromo-1H-indazole-carboxylate (4.0 g, 13.4 mmol) dissolved in 1,4- dioxane (130 mL), 2-chloro-3-pyridine boronic acid pinacol ester (4 g, 16.7 mmol), Pd(PPh3)4 (1.5 g, 1.3 mmol) and 2M aq. Na2CO3 (20 mL, 40 mmol) under nitrogen atmosphere. The rubber septum was replaced with reflux condenser containing three-way stopcock equipped with argon filled balloon. The reaction contents were stirred and air was removed from the closed reaction system by vacuum and back filled with argon. Following three cycles of degassing, the reaction mixture was heated at 100 C (oil-bath) under argon. Inflated argon balloon was emptied, refilled with argon and remounted in the course of reaction. The initial pale yellow heterogeneous reaction mixture turned to clear biphasic off-brown solution. After 18 h with no additional change in the proportion of the product (62%) as analyzed by LC/MS, the reaction mixture was cooled to room temperature. Upon concentration of the reaction mixture, EtOAc/water (200 mL / 75 mL) was transferred to the concentrate and stirred for 30 mm. The organic layer was separated and the aqueous layer extracted with EtOAc (100 mL X 2). Mg504 (20 g) and Celite (20 g) were added to combined organic layers and the contents suction filtered after stirring for 1 h. The filter cake was washed with EtOAc (300 mL) and the combined filtrates concentrated by rotary evaporator under vacuum. The crude concentrate was dissolved in in 1% MeOH/CH2C12 and absorbed on silica gel (20 g) by evaporating the solvent followed by drying. Subsequent purification by flash silica gel columnpurification of the dry powder (Combiflash companion system with RediSep silica gel column 120 g, 30-70%EtOAC/hexanes eluting solvent) provided 5-(2-chloropyridin-3-yl)-1H-indazole (1.5 g, 47%) as a white crystalline solid after concentration of the desired product fractions. 1H NMR (DMSO-d6): 13.2 (s, 1H), 8.41 (dd, 1H, J = 1.8 and 4.7 Hz), 8.13 (s, 1H), 7.90 (dd, 1H, J = 1.7 and 4.7 Hz), 7.84 (s, 1H), 7.62 (d, 1H, J = 8.8 Hz), 7.51 (dd, 1H, J = 4.7 and 7.3 Hz), 7.42 (dd, 1H, J = 1.4 and 8.5 Hz). LCMS: 95 %, MS (mle) 230 (MH+).
47% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃; for 18h;Inert atmosphere; A single necked round bottom flask containing a with a magnetic stir bar was charged with 5-bromo-1H-indazole (3.0 g, 15.2 mmol), di-tert-butyl dicarbonate (4.2 g, 19.2 mmol) and acetonitrile (30 mL) under mild stream of nitrogen at room temperature. Triethylamine (1.8 g, 2.5 mL, 17.7 mmol) was added in one portion to above stirred homogeneous solution followed by 4-(dimethylamino)pyridine (2.2 g, 18 mmol) over a period of 15 mm in portions. The homogenous off-brown clear reaction mixture was stirred at room temperature under nitrogen and the progress of reaction monitored by TLC (50% EtOAc/hexanes). Stirring was discontinued after 3h and the reaction mixture concentrated by rotary evaporator under vacuum. A clear viscous liquid was obtained and dissolved in EtOAc/hexanes (7:3, 200 mL), and diluted with water (75 mL). Organic layer was separated and the aqueous layer extracted with EtOAc/hexanes (1:1, 125 mL). The combined organic layers were washed with water (100 mL) followed by iN aq. HC1 (2 x 75mL) to remove 4-(dimethylamino)pyridine. The combined organic layers were washed with water (2 X 75 mL), saturated aq. NaHCO3 (2 X 75 mL) and saturated aqueous NaC1. Separated organic layers were dried over anhydrous Mg504, filtered, concentrated and dried under vacuum to provide tert-butyl 5-bromo-1H-indazole-carboxylate (4.5 g, purity 97%) as a pale yellow viscous liquid which was used without further purification. ?H NMR (DMSOd6): oe 8.36 (d, J 0.8 Hz, 1H), 8.11 (app d, J= 0.8 Hz, 1H), 8.00 (d, J= 8.8 Hz, 1H), 7.71 (app dd, J= 8.8, 0.8 Hz, 1H), 1.62 (s, 9H). LCMS: 97 %, MS (m/e) 241 (MHttBu). A single necked round bottom flask (250 mL) equipped with a magnetic stir bar was charged with tertbutyl 5-bromo-1H-indazole-carboxylate (4.0 g, 13.4 mmol) dissolved in 1,4-dioxane (130 mL), 2-chloro-3-pyridine boronic acid pinacol ester (4 g, 16.7 mmol), Pd(PPh3)4 (1.5 g, 1.3 mmol) and 2M aq.Na2CO3 (20 mL, 40 mmol) under nitrogen atmosphere. The rubber septum was replaced with reflux condenser containing three-way stopcock equipped with argon filled balloon. The reaction contents were stirred and air was removed from the closed reaction system by vacuum and back filled with argon. Following three cycles of degassing, the reaction mixture was heated at 100 C (oil-bath) under argon. Inflated argon balloon was emptied, refilled with argon and remounted in the course of reaction. The initial pale yellow heterogeneous reaction mixture turned to clear biphasic off-brown solution. After 18 h with no additional change in the proportion of the product (62%) as analyzed by LC/MS, the reaction mixture was cooled to room temperature. Upon concentration of the reaction mixture, EtOAc/water (200 mL / 75 mL) was transferred to the concentrate and stirred for 30 mm. The organic layer was separated and the aqueous layer extracted with EtOAc (100 mL X 2). Mg504 (20 g) and Celite (20 g) were added to combined organic layers and the contents suction filtered after stirring for 1 h. The filter cake was washed with EtOAc (300 mL) and the combined filtrates concentrated by rotary evaporator under vacuum. The crude concentrate was dissolved in in 1% MeOH/CH2C12 and absorbed on silica gel (20 g) by evaporating the solvent followed by drying. Subsequent purification by flash silica gel column purification of the dry powder (Combiflash companion system with RediSep silica gel column 120 g, 30-70% EtOAc/hexanes eluting solvent) provided 5-(2- chloropyridin-3-yl)-1H-indazole (1.5 g, 47%) as a white crystalline solid after concentration of the desired product fractions. ?H NMR (DMSO-d6): oe 13.2 (s, 1H), 8.41 (dd, J= 1.8 and 4.7 Hz, 1H), 8.13 (s, 1H), 7.90 (dd, J 4.7, 1.7 Hz, 1H), 7.84 (s, 1H), 7.62 (d, J= 8.8 Hz, 1H), 7.51 (dd, J= 7.3, 4.7 Hz, 1H), 7.42 (dd, J= 8.5, 1.4 Hz, 1H). LCMS: 95 %, MS (m/e)230 (MI-i?).
  • 21
  • [ 452972-11-1 ]
  • 2'-(4-fluoro-3-methylphenyl)-[3,3'-bipyridine]-6-carbonitrile [ No CAS ]
  • 22
  • [ 452972-11-1 ]
  • (2'-(4-Fluoro-3-methylphenyl)-[3,3'-bipyridin]-6-yl)methanamine [ No CAS ]
  • 23
  • [ 452972-11-1 ]
  • ethyl 2-(((2'-(4-fluoro-3-methylphenyl)-[3 ,3'-bipyridin]-6-yl)methyl)amino)-2-oxoacetate [ No CAS ]
  • 24
  • [ 452972-11-1 ]
  • N-((2'-(4-fluoro-3-methylphenyl)-[3,3'-bipyridin]-6-yl)methyl)formamide [ No CAS ]
  • 25
  • [ 452972-11-1 ]
  • ethyl 6-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)imidazo[1,5-a]pyridine-3-carboxylate [ No CAS ]
  • 26
  • [ 452972-11-1 ]
  • 6-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)imidazo[1,5-a]pyridine-3-carboxylic acid [ No CAS ]
  • 27
  • [ 452972-11-1 ]
  • 6-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)imidazo[1,5-a]pyridine [ No CAS ]
  • 28
  • tert-butyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-1-carboxylate [ No CAS ]
  • [ 452972-11-1 ]
  • 5-(2-chloropyridin-3-yl)-1H-pyrazolo[3,4-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); water; sodium carbonate; In 1,4-dioxane; at 100℃; for 12h;Inert atmosphere; General procedure: [0150j A single necked round bottom flask (250 mL) equipped with a magnetic stir bar was charged with tert-butyl 5-bromo-1H-indazole-carboxylate (4.0 g, 13.4 mmol) dissolved in 1,4- dioxane (130 mL), 2-chloro-3-pyridine boronic acid pinacol ester (4 g, 16.7 mmol), Pd(PPh3)4 (1.5 g, 1.3 mmol) and 2M aq. Na2CO3 (20 mL, 40 mmol) under nitrogen atmosphere. The rubber septum was replaced with reflux condenser containing three-way stopcock equipped with argon filled balloon. The reaction contents were stirred and air was removed from the closed reaction system by vacuum and back filled with argon. Following three cycles of degassing, the reaction mixture was heated at 100 C (oil-bath) under argon. Inflated argon balloon was emptied, refilled with argon and remounted in the course of reaction. The initial pale yellow heterogeneous reaction mixture turned to clear biphasic off-brown solution. After 18 h with no additional change in the proportion of the product (62%) as analyzed by LC/MS, the reaction mixture was cooled to room temperature. Upon concentration of the reaction mixture, EtOAc/water (200 mL / 75 mL) was transferred to the concentrate and stirred for 30 mm. The organic layer was separated and the aqueous layer extracted with EtOAc (100 mL X 2). Mg504 (20 g) and Celite (20 g) were added to combined organic layers and the contents suction filtered after stirring for 1 h. The filter cake was washed with EtOAc (300 mL) and the combined filtrates concentrated by rotary evaporator under vacuum. The crude concentrate was dissolved in in 1% MeOH/CH2C12 and absorbed on silica gel (20 g) by evaporating the solvent followed by drying. Subsequent purification by flash silica gel columnpurification of the dry powder (Combiflash companion system with RediSep silica gel column 120 g, 30-70%EtOAC/hexanes eluting solvent) provided 5-(2-chloropyridin-3-yl)-1H-indazole (1.5 g, 47%) as a white crystalline solid after concentration of the desired product fractions. [0152j 5-(2-chloropyridin-3-yl)-1H-pyrazolo[3,4-b]pyridine was prepared in the similar to the preparation of 5 -(2-chloropyridin-3 -yl)-l H-indazole by heating the mixture of tert-butyl 5- bromo- 1 H-pyrazolo [3 ,4-b]pyridine- 1 -carboxylate (2.0 g, 6.7 mmol), 2-chloro-3 -pyridine boronic acid pinacol ester (1.9 g, 8.0 mmol), Pd(PPh3)4 (770 mg, 67 mmol), 1,4-dioxane (40 mL) and2M aq. Na2CO3 (9 mL, 18 mmol) under argon atmosphere. After 12 h, the reaction mixture was cooled to room temperature and concentrated. The crude concentrate was diluted with EtOAc/water (200 mL / 100 mL), allowed to stir for 30 mm and the heterogeneous solution was filtered. The filter cake was washed with EtOAc (200 mL) and water (75 mL) successively. The filter cake thus obtained was analyzed as the desired product (0.55 g) and dissolved in a mixture of THF/MeOH (2:1, 50 mL). The homogeneous solution was passed through a pad of Celite and the filtrate concentrated to provide desired product as a crystalline solid (0.45 g). Organic layer from combined filtrates was separated, stirred with Mg504/Celite for 20 mm and filtered. The filtrate was concentrated and subjected to flash silica gel colunm purification (Combiflash companion system with RediSep silica gel column 12g , 30-50-9OEtOAC/hexanes eluting solvent gradient upon dry loading the sample by absorbing on silica gel) to obtain another 0.4 g of 5 -(2-chloropyridin-3 -yl)- 1 H-pyrazolo [3 ,4-b]pyridine. Total yield: 52%. ?H NMR (DMSO-d6):oe 13.83 (s, 1H), 8.59 (d, 1H, J = 2.0 Hz), 8.45 (dd, 1H, J = 1.7 and 4.7 Hz), 8.36 (d, 1H, J = 2.0 Hz), 8.21 (s, 1H), 8.00 (dd, 1H, J = 1.7 and 7.7 Hz), 7.59 (dd, 1H, J = 4.7 and 7.7 Hz). LCMS: rt 5.20 mm (A), purity 94 %, MS (mle) 231 (MHj.
  • 29
  • [ 312537-44-3 ]
  • [ 452972-11-1 ]
  • 6-(2-chloropyridin-3-yl)benzo[d]oxazol-2(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); water; sodium carbonate; In 1,4-dioxane; at 100℃; for 12h;Inert atmosphere; General procedure: [0150j A single necked round bottom flask (250 mL) equipped with a magnetic stir bar was charged with tert-butyl 5-bromo-1H-indazole-carboxylate (4.0 g, 13.4 mmol) dissolved in 1,4- dioxane (130 mL), 2-chloro-3-pyridine boronic acid pinacol ester (4 g, 16.7 mmol), Pd(PPh3)4 (1.5 g, 1.3 mmol) and 2M aq. Na2CO3 (20 mL, 40 mmol) under nitrogen atmosphere. The rubber septum was replaced with reflux condenser containing three-way stopcock equipped with argon filled balloon. The reaction contents were stirred and air was removed from the closed reaction system by vacuum and back filled with argon. Following three cycles of degassing, the reaction mixture was heated at 100 C (oil-bath) under argon. Inflated argon balloon was emptied, refilled with argon and remounted in the course of reaction. The initial pale yellow heterogeneous reaction mixture turned to clear biphasic off-brown solution. After 18 h with no additional change in the proportion of the product (62%) as analyzed by LC/MS, the reaction mixture was cooled to room temperature. Upon concentration of the reaction mixture, EtOAc/water (200 mL / 75 mL) was transferred to the concentrate and stirred for 30 mm. The organic layer was separated and the aqueous layer extracted with EtOAc (100 mL X 2). Mg504 (20 g) and Celite (20 g) were added to combined organic layers and the contents suction filtered after stirring for 1 h. The filter cake was washed with EtOAc (300 mL) and the combined filtrates concentrated by rotary evaporator under vacuum. The crude concentrate was dissolved in in 1% MeOH/CH2C12 and absorbed on silica gel (20 g) by evaporating the solvent followed by drying. Subsequent purification by flash silica gel columnpurification of the dry powder (Combiflash companion system with RediSep silica gel column 120 g, 30-70%EtOAC/hexanes eluting solvent) provided 5-(2-chloropyridin-3-yl)-1H-indazole (1.5 g, 47%) as a white crystalline solid after concentration of the desired product fractions. [01 57j Analogous to the preparation of 5 -(2-chloropyridin-3 -yl)- 1 H-indazole,6-(2- chloropyridin-3 -yl)benzo [d]oxazol-2(3H)-one was prepared by heating the mixture of 1 -trityl-6- bromo-2-benzoxazilinone (2.0 g, 4.4 mmol), 2-chloro-3-pyridine boronic acid pinacol ester (1.3 g, 5.4 mmol), Pd(PPh3)4 (0.5 g, 0.43 mmol) and 2M aq. Na2CO3 (8 mL, 16 mmol) in 1,4-dioxane (75 mL) under argon atmosphere for 12 h. LC/MS indicated three products with MH 489, 245 and 566. Extractive work-up followed by flash silica gel column purification (Combiflash companion system with RediSep silica gel column 40 g , 20-70%EtOAC/hexanes eluting solvent gradient upon dry loadingthe concentrate absorbed on silica gel) provided 6-(2- chloropyridin-3-yl)benzo[d]oxazol-2(3H)-one (0.44 g, 38%) as an off-white solid after concentration of the respective product fractions. LCMS: rt 5.85 mm (A), purity 94 %, MS (mle) 247 (MHj.
  • 30
  • [ 590417-94-0 ]
  • [ 452972-11-1 ]
  • 6-(2-chloropyridin-3-yl)-1-methyl-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃; for 12h;Inert atmosphere; General procedure: [0150j A single necked round bottom flask (250 mL) equipped with a magnetic stir bar was charged with tert-butyl 5-bromo-1H-indazole-carboxylate (4.0 g, 13.4 mmol) dissolved in 1,4- dioxane (130 mL), 2-chloro-3-pyridine boronic acid pinacol ester (4 g, 16.7 mmol), Pd(PPh3)4 (1.5 g, 1.3 mmol) and 2M aq. Na2CO3 (20 mL, 40 mmol) under nitrogen atmosphere. The rubber septum was replaced with reflux condenser containing three-way stopcock equipped with argon filled balloon. The reaction contents were stirred and air was removed from the closed reaction system by vacuum and back filled with argon. Following three cycles of degassing, the reaction mixture was heated at 100 C (oil-bath) under argon. Inflated argon balloon was emptied, refilled with argon and remounted in the course of reaction. The initial pale yellow heterogeneous reaction mixture turned to clear biphasic off-brown solution. After 18 h with no additional change in the proportion of the product (62%) as analyzed by LC/MS, the reaction mixture was cooled to room temperature. Upon concentration of the reaction mixture, EtOAc/water (200 mL / 75 mL) was transferred to the concentrate and stirred for 30 mm. The organic layer was separated and the aqueous layer extracted with EtOAc (100 mL X 2). Mg504 (20 g) and Celite (20 g) were added to combined organic layers and the contents suction filtered after stirring for 1 h. The filter cake was washed with EtOAc (300 mL) and the combined filtrates concentrated by rotary evaporator under vacuum. The crude concentrate was dissolved in in 1% MeOH/CH2C12 and absorbed on silica gel (20 g) by evaporating the solvent followed by drying. Subsequent purification by flash silica gel columnpurification of the dry powder (Combiflash companion system with RediSep silica gel column 120 g, 30-70%EtOAC/hexanes eluting solvent) provided 5-(2-chloropyridin-3-yl)-1H-indazole (1.5 g, 47%) as a white crystalline solid after concentration of the desired product fractions. [01 59j Analogous to the preparation of 5 -(2-chloropyridin-3 -yl)- 1 H-indazole,6-(-2-chloropyridin-3 -yl)- i-methyl-i H-indazole was prepared by heating the mixture of 6-bromo- 1-methyl-1H-indazole (2.0 g, 9.5 mmol), 2-chloro-3-pyridine boronic acid pinacol ester (2.2 g, 9.4 mmol), Pd(PPh3)4 (0.54 g, 0.46 mmol) and 2M aq. Na2CO3 (14 mL, 28 mmol) in 1,4-dioxane (75 mL) under argon atmosphere for 12 h. Upon extractive work-up as discussed in the preparation of of 5 -(2-chloropyridin-3 -yl)-l H-indazole with CH2C12 and purification of the concentrate by flash silica gel column chromatography (Combiflash companion system with RediSep silica gel column 40 g, 30-50%EtOAC/hexanes eluting solvent gradient upon dry loadingthe concentrate absorbed on silica gel) provided 6-(-2-chloropyridin-3-yl)-1-methyl-1H-indazole as a white solid (1.8 g, 77%).?H NMR (DMSO-d6): oe 8.45 (dd, 1H, J = 1.7 and 4.7 Hz), 8.09 (s, 1H), 7.94 (dd, 1H, J = 2.0 and 7.6 Hz), 7.82 (d, 1H, J = 8.5 Hz), 7.74 (s, 1H), 7.54 (dd, 1H, J = 4.7 and7.6 Hz),7.22 (d, 1H, J = 8.5 Hz), 4.06 (s, 3H). LCMS: rt 6.80 mm (A), purity 97 %, MS (mle)244 (MHj.
  • 31
  • [ 321-23-3 ]
  • [ 452972-11-1 ]
  • C11H6ClFN2O2 [ No CAS ]
  • 32
  • [ 97483-77-7 ]
  • [ 452972-11-1 ]
  • C11H6ClN3 [ No CAS ]
  • 33
  • 6-chloro-4-methoxypyrido[3,2-d]pyrimidine [ No CAS ]
  • [ 452972-11-1 ]
  • 6-(2-chloropyridin-3-yl)-4-methoxypyrido[3,2-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.25 g With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 98℃;Inert atmosphere; [0449j 6-(2-Chloropyridin-3 -yl)-4-methoxypyrido [3 ,2-d]pyrimidine. A reaction flask was charged 6-chloro-4-methoxypyrido [3 ,2-d]pyrimidine (3.5 g, 17.8 mmol), 2-chloro-3 - pyridineboronic acid pinacol ester (4.35 g, 18.2 mmol), Na2CO3 (4.0 g, 38.2 mmol) and 1,4- dioxane (100 mL) and a stir bar. The contents were degassed by vacuum and back filled with argon three times while stirring. Subsequently, Pd(PPh3)3 (0.87 g, 0.75 mmol) was added to the reaction contents, repeated degassing cycles and heated under argon at 98 C. The heating was stopped after overnight, the yellow hot heterogeneous reaction mixture was suction filtered on a Buchner funnel and washed the cake with additional amount of dioxane (30 mL). The pale yellow clear filtrate solution was passed through a pad of Celite and concentrated the filtrate. The crude pale yellow solid residue was partitioned between CH2C12 (150 mL)/water (50 mL). The organic layer was separated, dried over Mg504, filtered and concentrated. The crude concentrate was stirred in EtOAc (30 mL) and suction filtered. The filter cake was washed further with EtOAc (10 mL) and dried to obtain 1.6 g of 6-(2-chloropyridin-3-yl)-4-methoxypyrido [3 ,2-d]pyrimidine (purity: 95%) as a white solid. The filtrate was concentrated and purified the concentrate by flash column chromatography (Combiflash companion system with RediSep silica gel column 40 g, 0-30-60% EtOAC/hexanes eluting solvent gradient) to obtain additional 0.65 g of titled compound. ?H NMR (300 MHz, DMSO-d6): oe 8.92 (s, 1H), 8.57 (dd, J 4.8, 2.0 Hz, 1H), 8.45 (d, J 8.7 Hz, 1H), 8.28 (d, J 8.7 Hz, 1H), 8.13 (dd, J 7.6, 2.0 Hz, 1H), 7.63 (dd, J= 7.6, 4.8 Hz, 1H), 4.16 (s, 3H).
1.6 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water;Inert atmosphere; 6-(2-Chloropyridin-3-yl)-4-methoxypyrido 13,2-d1 pyrimidine: A reaction flask was charged 6-chloro-4-methoxypyrido [3 ,2-dj pyrimidine (3.5 g, 17.8 mmol), 2-chloro-3 - pyridineboronic acid pinacol ester (4.35 g, 18.2 mmol), Na2CO3 (4.0 g, 38.2 mmol) and 1,4- dioxane (100 mL) and a stir bar. The contents were degassed by vacuum and back filled with argon three times while stirring. Subsequently, Pd(PPh3)3 (0.87 g, 0.75 mmol) was added to the reaction contents, repeated degassing cycles, and heated for overnight under argon at 98C. The yellow heterogeneous reaction mixture was cooled to room temperature and suction filtered on a Buchner funnel. The collected solid on the funnel was washed with additional amount of dioxane (30 mL). The pale yellow clear filtrate solution was passed through a pad of Celite and concentrated. The cmde pale yellow solid residue thus obtained was partitioned between CH2C12 (150 mL)/water (50 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated. The cmde concentrate was stirred in EtOAc (30 mL) and suction filtered. The filter cake was washed with EtOAc (10 mL) and dried to obtain 1.6 g of 6-(2-chloropyridin-3 -yl)-4-methoxypyrido[3 ,2-dj pyrimidine (purity: 95%) as a white solid. The filtrate was concentrated and purified the concentrate by flash column chromatography (Combiflash companion system with RediSep silica gel column 40 g, 0- 30-60% EtOAC/hexanes eluting solvent gradient) to obtain additional 0.65 g of titled compound. ?H NMR (300 MHz, DMSO-d6): oe 8.92 (s, 1H), 8.57 (dd, J= 4.8, 2.0 Hz, 1H), 8.45 (d, J 8.7 Hz, 1H), 8.28 (d, J 8.7 Hz, 1H), 8.13 (dd, J 7.6, 2.0 Hz, 1H), 7.63 (dd, J7.6, 4.8 Hz, 1H), 4.16 (s, 3H).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 452972-11-1 ]

Organoborons

Chemical Structure| 865186-94-3

A217124 [865186-94-3]

3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.83

Chemical Structure| 329214-79-1

A221423 [329214-79-1]

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.82

Chemical Structure| 444120-94-9

A296629 [444120-94-9]

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.79

Chemical Structure| 1171891-31-8

A316389 [1171891-31-8]

4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.77

Chemical Structure| 1012085-50-5

A104715 [1012085-50-5]

3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.76

Chlorides

Chemical Structure| 865186-94-3

A217124 [865186-94-3]

3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.83

Chemical Structure| 444120-94-9

A296629 [444120-94-9]

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.79

Chemical Structure| 408492-27-3

A204328 [408492-27-3]

2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.74

Chemical Structure| 381248-04-0

A176642 [381248-04-0]

(2-Chloropyridin-3-yl)boronic acid

Similarity: 0.73

Chemical Structure| 1073353-78-2

A111660 [1073353-78-2]

2,3-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.72

Related Parent Nucleus of
[ 452972-11-1 ]

Pyridines

Chemical Structure| 865186-94-3

A217124 [865186-94-3]

3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.83

Chemical Structure| 329214-79-1

A221423 [329214-79-1]

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.82

Chemical Structure| 444120-94-9

A296629 [444120-94-9]

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.79

Chemical Structure| 1171891-31-8

A316389 [1171891-31-8]

4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.77

Chemical Structure| 1012085-50-5

A104715 [1012085-50-5]

3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.76