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Chemical Structure| 38186-84-4 Chemical Structure| 38186-84-4
Chemical Structure| 38186-84-4

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CAS No.: 38186-84-4

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Product Details of [ 38186-84-4 ]

CAS No. :38186-84-4
Formula : C6H5ClFN
M.W : 145.56
SMILES Code : ClC1=NC=C(C=C1C)F
MDL No. :MFCD04972725
InChI Key :FMPYGEFGXUAAKG-UHFFFAOYSA-N
Pubchem ID :12852014

Safety of [ 38186-84-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Calculated chemistry of [ 38186-84-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.17
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 34.17
TPSA ?

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

12.89 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

1.89
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

2.28
Log Po/w (WLOGP)?

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

2.6
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.

1.85
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

2.88
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.3

Water Solubility

Log S (ESOL):?

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

-2.67
Solubility 0.31 mg/ml ; 0.00213 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.

-2.19
Solubility 0.945 mg/ml ; 0.00649 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

-3.29
Solubility 0.0755 mg/ml ; 0.000519 mol/l
Class?

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

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

No
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

Yes
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

No
Log Kp (skin permeation)?

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

-5.57 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

2.0
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

1.0 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)

1.62

Application In Synthesis of [ 38186-84-4 ]

* 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 [ 38186-84-4 ]

[ 38186-84-4 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 72716-93-9 ]
  • [ 38186-84-4 ]
  • [ 109-76-2 ]
  • [ 92992-84-2 ]
  • [ 92992-83-1 ]
  • 2
  • [ 38186-84-4 ]
  • [ 109-76-2 ]
  • [ 92992-81-9 ]
  • [ 92992-82-0 ]
  • N,N'-Bis-(5-fluoro-3-methyl-pyridin-2-yl)-propane-1,3-diamine [ No CAS ]
  • 3
  • [ 38186-82-2 ]
  • [ 38186-84-4 ]
  • 4
  • [ 38186-82-2 ]
  • [ 54232-03-0 ]
  • [ 38186-84-4 ]
  • 5
  • [ 111-34-2 ]
  • [ 38186-84-4 ]
  • [ 1211535-74-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate;palladium diacetate; 1,3-bis-(diphenylphosphino)propane; In methanol; at 20 - 130℃; for 20h; A. 7-(5 -Fluoro-3 -methylpyridin-2-yl)-N-(5 -(trifluoromethyl)pyrimidin-2-yl)- 1 , 8 -naphthyridin-4- amine (compound 1)1. 2-Acetyl-5-fluoro-3-methylpyridine Dissolve 2-chloro-5 -fluoro-3 -methylpyridine (1.45 g, 0.01 moles) in MeOH (30 mL) at room temperature. Add butylvinylether (3.0 mL) and NaHCO3 (3.0 g) to the reaction mixture and degas with nitrogen for 5 minutes. Add catalyst Pd(OAc)2 (120 mg) and 1,3- bis(diphenylphosphino)propane (360 mg) to the mixture and then heat at 13O0C in a pressure vessel with stirring for 20 hours. Cool the reaction mixture to room temperature and remove the insoluble EPO <DP n="50"/>material by filtration. Wash the solid with MeOH (25 mL) and then add 5.0 mL of 6.0 N aqueous HCl to the filtrate. Stir the mixture at room temperature for 20 hours. Concentrate the reaction mixture under vacuum, dilute it with EtOAc (100 mL), wash the organic layer with aq. Na2CO3 (2 x 50 mL) and dry (MgSO4). Filter the dried extract and concentrate under vacuum to afford crude product as pink oil. Purify the crude product by column chromatography to afford pure product as colorless oil.
  • 6
  • [ 38186-84-4 ]
  • [ 886365-56-6 ]
YieldReaction ConditionsOperation in experiment
55.2% To a solution of <strong>[38186-84-4]2-chloro-5-fluoro-3-methylpyridine</strong> D38 (0.50 g, 2.82 mmol) in dry toluene (12.5 ml) were added sodium t-butoxyde (0.462 g, 4.81 mmol), Pd2(dba)3 (0.315 g, 0.344 mmol), BINAP (0.642 g, 1.031 mmol) and benzophenone imine (0.692 ml, 4.12 mmol). The resulting mixture was degassed (3.x.pump/N2) and then heated to 80° C. After 1 h stirring, the mixture was cooled down to room temperature, diluted with Et2O (400 ml) and filtered through a celite pad. Volatiles were evaporated, the resulting oil was dissolved in THF (34 ml) and HCl (1.408 ml of a 2 M aqueous solution, 2.82 mmol) was added. The mixture was stirred at room temperature for 1.5 h, then neutralized with a saturated NaHCO3 aqueous solution and diluted with DCM (200 ml). The inorganic layer was back-extracted with DCM (2.x.50 ml). The collected organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (Biotage SP4 12M, Cy/EtOAc 60/40). Collected fractions gave the title compound D39 (0.20 g, 1.554 mmol, 55.2percent yield from D38, two steps), as an orange solid. MS: (ES/+) m/z: 127 (M+1). C6H7FN2 requires 126.1H NMR (400 MHz, DMSO-d6) delta(ppm): 7.73 (d, 1H), 7.23 (dd, 1H), 5.60 (bs, 2H), 2.04 (s, 3H).
5-Fluoro-3-methyl-2-pyridinamine (DIl): To a solution of <strong>[38186-84-4]2-chloro-5-fluoro-3-methylpyridine</strong> DlO (0.50 g) in dry toluene (12.5 ml) were added sodium t-butoxyde (0.462 g, 4.81 mmol), Pd2(dba)3 (0.315 g, 0.344 mmol), BINAP (0.642 g, 1.031 mmol) and benzophenone imine (0.692 ml, 4.12 mmol). The resulting mixture was degassed (3 x pump/N2) and then heated to 80 0C. After 1 hour stirring, the mixture was cooled down to room temperature, diluted with Et2O (400 ml) and filtered through a celite pad. Volatiles were evaporated, the resulting oil was dissolved in THF (34 ml) and HCl (1.408 ml of a 2 M aqueous solution, 2.82 mmol) was added. The mixture was stirred at room temperature for 1.5 hours, then neutralized with a saturated NaHCO3 aqueous solution and diluted with DCM (200 ml). The inorganic layer was back- extracted with DCM (2 x 50 ml). The collected organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (Biotage SP4 12M column, Cy/EtOAc 60/40). Collected fractions gave the title compound DIl (0.20 g) as an orange solid. MS: (ES/+) m/z: 127 (M+l). C6H7FN2 requires 126. 1H NMR (400 MHz, DMSO-J6) delta ppm: 7.73 (d, 1 H), 7.23 (dd, 1 H), 5.60 (bs, 2 H), 2.04 (s, 3 H).
  • 7
  • [ 1097264-82-8 ]
  • [ 38186-84-4 ]
YieldReaction ConditionsOperation in experiment
To an ice-cooled mixture of the crude mesylate (4.53 g, 18.90 mmol) in THF (180 ml), LAH (18.90 ml of a 1.0 M solution in THF, 18.90 mmol) was added dropwise and the reaction was stirred for 1 h. A 2 M HCl aqueous solution (80 ml) was added, the resulting mixture stirred for 30 min and then DCM (400 ml) was added. The organic layer was separated and evaporated to give the title compound D38 (2.28 g, 12.84 mmol, 67.9percent yield from (2-chloro-5-fluoro-3-pyridinyl)methanol, two steps) as a white solid.HPLC (walk-up): rt=3.56 min.1H NMR (400 MHz, DMSO-d6) delta (ppm): 8.31 (d, 1H), 7.86 (dd, 1H), 2.35 (s, 3H).
With lithium aluminium tetrahydride; In tetrahydrofuran;Cooling; To a -20 0C cooled solution of (2-chloro-5-fluoro-3-pyridinyl)methanol (3.086 g, 19.10 mmol) and TEA (5.32 ml, 38.20 mmol) in anhydrous DCM (180 ml), MsCl (2.233 ml, 28.70 mmol) was added dropwise and the resulting reaction mixture stirred at 0 0C for 30 minutes. Volatiles were evaporated under reduced pressure to afford the desired mesylate (4.53 g) that was used in the next step without further purification. [Mesylate data: MS: (ES/+) m/z: 240 (M+l) and 242 (M+l). C7H7ClFNO3S requires 239]. To an ice-cooled mixture of the crude mesylate (4.53 g, 18.90 mmol) in THF (180 ml), LAH (18.90 ml of a 1.0 M solution in THF, 18.90 mmol) was added dropwise and the reaction was stirred for 1 hour. A 2 M HCl aqueous solution (80 ml) was added, the resulting mixture stirred for 30 minutes and then DCM (400 ml) was added. The organic layer was separated and evaporated to give the title compound DlO (2.28 g) as a white solid. HPLC (walk-up): rt = 3.56 min. 1H NMR (400 MHz, DMSO-J6) delta ppm: 8.31 (d, 1 H), 7.86 (dd, 1 H), 2.35 (s, 3 H).
  • 8
  • [ 557-21-1 ]
  • [ 38186-84-4 ]
  • [ 1261883-35-5 ]
YieldReaction ConditionsOperation in experiment
tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 120℃; for 0.5h;microwave irradiation; Acid-22: 5-Fluoro-3-methyl-pyridine-2-carboxylic acid; a) 5-Fluoro-3-methyl-pyridine-2-carbonitrile; A soln. of <strong>[38186-84-4]2-chloro-5-fluoro-3-methyl-pyridine</strong> (CAS 38186-84-4, 408 mg, 2.750 mmol), Zn(CN)2 (230 mg, 1.923 mmol) and Pd(PPh3)4 (190 mg, 0.165 mmol) in DMF (8 ml) was stirred at 120 C for 0.5 h in a microwave. The reaction mixture was filtered over hyflo, diluted with TBME and H20 and extracted with brine. The aq. phases were reextracted with TBME, the combined org. phases were dried over Na2S04, filtered and concentrated. Flash chromatography on silica gel (hexane-EtOAc 100:0 to 80:20) yielded the title compound. HPLC: 0.72 min; 1 H NMR (400 MHz, CDCI3): delta 8.42 (d, 1 H), 7.42-7.39 (m, 1 H), 2.61 (s, 3H).
  • 9
  • [ 38186-84-4 ]
  • C10H13FN2O3 [ No CAS ]
  • 10
  • [ 38186-84-4 ]
  • 5-fluoro-3-methyl-pyridin-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% With hydrogenchloride; at 150℃; for 15h;Microwave irradiation; <strong>[38186-84-4]2-chloro-5-fluoro-3-methylpyridine</strong> (lg, 6.870 mmol) is dissolved in hydrochloric acid(37percent, 20 mL) and the reaction is heated under microwave irradiation at 15000 for15h. The mixture is diluted with water and washed with DCM. The aqueous layer isbasified with NaOH and re-extracted with DCM several times. The organic layer isseparated, dried and evaporated to furnish 5-fluoro-3-methyl-pyridin-2-ol (140 mg,content 74percent, 12percent).UPLC-MS (Method 2): R = 0.50 mmMS (ESI pos): mlz = 128 (M+H)+
With hydrogenchloride; water; at 150℃; for 15h;Microwave irradiation; 10365] <strong>[38186-84-4]2-chloro-5-fluoro-3-methylpyridine</strong> (1 g, 6.870 mmol) is dissolved in hydrochloric acid (37percent, 20 mE) and the reaction is heated under microwave irradiation at 150° C. for 15 h. The mixture is diluted with water and washed with DCM. The aqueous layer is basified with NaOH and reextracted with DCM several times. The organic layer is separated, dried and evaporated to thrnish 5-fluoro-3-methyl-py-ridin-2-ol (140 mg, content 74percent, 12percent).10366] UPEC-MS (Method 2): R=0.50 mm10367] MS (ESI pos): mlz=128 (M+H)
  • 11
  • ethyl 4-([8-fluoro-1-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-yl]oxy}methyl)piperidine-4-carboxylate [ No CAS ]
  • [ 38186-84-4 ]
  • ethyl 4-([8-fluoro-1-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-yl]oxy}methyl)-1-(5-fluoro-3-methylpyridin-2-yl)piperidine-4-carboxylate [ No CAS ]
  • 12
  • [ 38186-84-4 ]
  • 2-chloro-5-fluoro-3-methyl-4-nitropyridine 1-oxide [ No CAS ]
  • 13
  • [ 38186-84-4 ]
  • ethyl 3-(3,7-dimethyl-3H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-3-(3-(hydroxymethyl)-4-methylphenyl)propanoate [ No CAS ]
  • 14
  • [ 38186-84-4 ]
  • 2-chloro-5-fluoro-3-methylpyridine 1-oxide [ No CAS ]
  • 15
  • [ 38186-84-4 ]
  • 2-chloro-3-methyl-5-(methylamino)-4-nitropyridine 1-oxide [ No CAS ]
  • 16
  • [ 38186-84-4 ]
  • 6-chloro-N3,5-dimethylpyridine-3,4-diamine [ No CAS ]
  • 17
  • [ 38186-84-4 ]
  • 6-chloro-3,7-dimethyl-3H-[1,2,3]triazolo[4,5-c]pyridine [ No CAS ]
  • 18
  • [ 38186-84-4 ]
  • (E)-ethyl 3-(3,7-dimethyl-3H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)acrylate [ No CAS ]
  • 19
  • [ 110-85-0 ]
  • [ 38186-84-4 ]
  • 1-(5-fluoro-6-methylpyridin-2-yl)piperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% In ethanol; at 145 - 155℃; for 3h;Inert atmosphere; 2-Chloro-5-fluoro-3-methylpyridine (1 .Og, 6.9 mmol) was added under nitrogen at 20°C to piperazine (3.0 g, 34 mmol) in ethanol (30 ml). The ethanol was partially distilled off and the solution heated at 155 °C (130 °C internal) using an air condenser for one hour and allowed to cool. The reaction was heated for a further 2 hours at 145 °C for complete conversion. The cooled residue was stirred with water (10 ml) to give an orange solution and pale crystalline solid. The product was partitioned between DCM (30 ml) and water (10 ml). The layers were separated and the aqueous was extracted with DCM (4 x 10 ml). The combined organics were concentrated in vacuo and purified via flash column chromatography: elution with 5 column volumes of MTBE removed the starting halide; further elution with 10:4:1 MTBE / MeOH / NH3 (35percent aq) afforded fractions containing product. The fractions were reduced in vacuo to afford the title compound as a yellow oil which crystallised on standing (706 mg, 53 percent).1H NIVIR (500 MHz, Methanol-d4) 7.26 (t, J = 9.0 Hz, 1H), 6.59 (dd, J = 9.0, 2.6 Hz, 1H), 3.44? 3.38 (m, 4H), 2.93 ? 2.89 (m, 4H), 2.33 (d, J = 3.0 Hz, 3H). LCMS Method 2 - Tr = 0.98 mm (ES+) (M+H)+ 196
  • 20
  • [ 38186-84-4 ]
  • (S)-3-((1R,3R)-1-(2-(2-((tert-butoxycarbonyl)(3-fluoropropyl)amino)ethoxy)-5-fluoro-3-methylpyridin-4-yl)-3-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)-2-methylpropanoic acid [ No CAS ]
  • 21
  • [ 38186-84-4 ]
  • (S)-3-((1R,3R)-1-(5-fluoro-2-(2-((3-fluoropropyl)amino)ethoxy)-3-methylpyridin-4-yl)-3-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)-2-methylpropanoic acid [ No CAS ]
  • 22
  • [ 38186-84-4 ]
  • methyl (S)-3-((1R,3R)-1-(2-chloro-5-fluoro-3-methylpyridin-4-yl)-3-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)-2-methylpropanoate [ No CAS ]
  • 23
  • [ 38186-84-4 ]
  • (R)-3-((1R,3R)-1-(5-fluoro-2-(2-((3-fluoropropyl)amino)ethoxy)-3-methylpyridin-4-yl)-3-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)-2-methylpropanoic acid [ No CAS ]
  • 24
  • [ 38186-84-4 ]
  • methyl (R)-3-((1R,3R)-1-(2-chloro-5-fluoro-3-methylpyridin-4-yl)-3-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)-2-methylpropanoate [ No CAS ]
  • 25
  • [ 38186-84-4 ]
  • methyl (R)-3-((1R,3R)-1-(2-(2-((tert-butoxycarbonyl)(3-fluoropropyl)amino)ethoxy)-5-fluoro-3-methylpyridin-4-yl)-3-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)-2-methylpropanoate [ No CAS ]
  • 26
  • [ 38186-84-4 ]
  • (R)-3-((1R,3R)-1-(2-(2-((tert-butoxycarbonyl)(3-fluoropropyl)amino)ethoxy)-5-fluoro-3-methylpyridin-4-yl)-3-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)-2-methylpropanoic acid [ No CAS ]
  • 27
  • [ 38186-84-4 ]
  • (R)-3-((1R,3R)-1-(5-fluoro-2-(2-((3-fluoropropyl)(methyl)amino)ethoxy)-3-methylpyridin-4-yl)-3-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)-2-methylpropanoic acid [ No CAS ]
  • 28
  • [ 107-31-3 ]
  • [ 38186-84-4 ]
  • 2-chloro-5-fluoro-3-methylisonicotinaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% LDA solution (2M, 3.85 mL, 7.70 mmol) was added to a cooled solution of <strong>[38186-84-4]2-chloro-5-fluoro-3-methylpyridine</strong> (1.02 g, 7.00 mmol) in THF (22.9 mL) at -78 °C. The reaction was stirred for30 mm, then methyl formate (1 .30 mL, 21.0 mmol) was added and the reaction was stirred fora further 30 minutes. The reaction was quenched by addition of iN HC1 solution (20 mL) andextracted with EtOAc (40 mL). The organic phase was washed with saturated aqueous sodiumchloride, dried over Na2SO4 and evaporated. The crude product was purified by flash silicachromatography, elution gradient 0 to 20percent EtOAc in heptane. Product containing fractions were evaporated to dryness to afford 2-chloro-5 -fluoro-3 -methylisonicotinaldehyde (754 mg, 62percent)as a straw coloured liquid. ?HNMR (500 MHz, CDC13, 27°C) 2.65 (3H, s), 8.33 (1H, s), 10.51 (1H, s).
  • 29
  • [ 38186-84-4 ]
  • 5-chloro-3,6-dimethyl-1H-pyrazolo[4,3-b]pyridine [ No CAS ]
 

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Similarity: 0.80

Chemical Structure| 214045-86-0

A124965 [214045-86-0]

1-Chloro-6-fluoroisoquinoline

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Chlorides

Chemical Structure| 851484-95-2

A103028 [851484-95-2]

2-Chloro-5-fluoronicotinaldehyde

Similarity: 0.86

Chemical Structure| 791644-48-9

A162319 [791644-48-9]

2-Chloro-5-fluoronicotinonitrile

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Chemical Structure| 31301-51-6

A361482 [31301-51-6]

2-Chloro-5-fluoropyridine

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Chemical Structure| 881891-83-4

A110342 [881891-83-4]

2-Chloro-5-fluoro-4-methylpyridine

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Chemical Structure| 69042-30-4

A791173 [69042-30-4]

1-Chloro-2,7-naphthyridine

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Related Parent Nucleus of
[ 38186-84-4 ]

Pyridines

Chemical Structure| 851484-95-2

A103028 [851484-95-2]

2-Chloro-5-fluoronicotinaldehyde

Similarity: 0.86

Chemical Structure| 791644-48-9

A162319 [791644-48-9]

2-Chloro-5-fluoronicotinonitrile

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Chemical Structure| 31301-51-6

A361482 [31301-51-6]

2-Chloro-5-fluoropyridine

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Chemical Structure| 881891-83-4

A110342 [881891-83-4]

2-Chloro-5-fluoro-4-methylpyridine

Similarity: 0.80

Chemical Structure| 884494-50-2

A436300 [884494-50-2]

2-Chloro-5-fluoro-4-iodo-3-methylpyridine

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