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Chemical Structure| 17201-43-3 Chemical Structure| 17201-43-3
Chemical Structure| 17201-43-3

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CAS No.: 17201-43-3

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Product Citations

Product Citations

Zehuan Huang ; Xiaoyi Chen ; Stephen J. K. O’Neill ; Guanglu Wu ; Daniel J. Whitaker ; Jiaxuan Li , et al.

Abstract: Supramolecular polymer networks are non-covalently crosslinked soft materials that exhibit unique mechanical features such as self-healing, high toughness and stretchability. Previous studies have focused on optimizing such properties using fast-dissociative crosslinks (that is, for an aqueous system, dissociation rate constant kd?>?10?s?1). Herein, we describe non-covalent crosslinkers with slow, tuneable dissociation kinetics (kd?

Purchased from AmBeed: ; ; ; ; ; ;

Alternative Products

Product Details of [ 17201-43-3 ]

CAS No. :17201-43-3
Formula : C8H6BrN
M.W : 196.04
SMILES Code : C1=CC(=CC=C1C#N)CBr
MDL No. :MFCD00001829
InChI Key :UMLFTCYAQPPZER-UHFFFAOYSA-N
Pubchem ID :86996

Safety of [ 17201-43-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501
Class:8
UN#:3261
Packing Group:Ⅱ

Calculated chemistry of [ 17201-43-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 43.99
TPSA ?

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

23.79 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

2.02
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

2.14
Log Po/w (WLOGP)?

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

2.3
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.

2.25
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

2.81
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.

-2.78
Solubility 0.324 mg/ml ; 0.00165 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.

-2.27
Solubility 1.05 mg/ml ; 0.00535 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

-3.74
Solubility 0.0353 mg/ml ; 0.00018 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.

-5.98 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)

 1.95

Application In Synthesis of [ 17201-43-3 ]

* 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 [ 17201-43-3 ]

[ 17201-43-3 ] Synthesis Path-Downstream   1~28

  • 1
  • [ 66389-77-3 ]
  • [ 17201-43-3 ]
  • [ 66389-80-8 ]
  • 2
  • [ 41602-56-6 ]
  • [ 17201-43-3 ]
  • [ 101046-16-6 ]
  • 3
  • [ 17201-43-3 ]
  • [ 252061-66-8 ]
  • [ 252061-67-9 ]
  • 4
  • [ 123-75-1 ]
  • [ 103-71-9 ]
  • [ 17201-43-3 ]
  • [ 774-07-2 ]
  • 4-(2,4-dioxo-3-phenyl-7-pyrrolidin-1-yl-3,4-dihydro-2<i>H</i>-pyrimido[4,5-<i>d</i>]pyrimidin-1-ylmethyl)-benzonitrile [ No CAS ]
  • 5
  • [ 123-75-1 ]
  • [ 16744-98-2 ]
  • [ 17201-43-3 ]
  • [ 774-07-2 ]
  • 4-[3-(2-fluorophenyl)-2,4-dioxo-7-pyrrolidin-1-yl-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-2-ylmethyl]benzonitrile [ No CAS ]
  • 6
  • [ 123-75-1 ]
  • [ 56753-76-5 ]
  • [ 17201-43-3 ]
  • [ 774-07-2 ]
  • 2-[1-(4-cyano-benzyl)-2,4-dioxo-7-pyrrolidin-1-yl-1,4-dihydro-2<i>H</i>-pyrimido[4,5-<i>d</i>]pyrimidin-3-yl]-3-phenyl-propionic acid methyl ester [ No CAS ]
  • 7
  • [ 123-00-2 ]
  • [ 87543-80-4 ]
  • [ 17201-43-3 ]
  • [ 774-07-2 ]
  • ethyl 2-[1-(4-cyanobenzyl)-7-(3-morpholin-4-yl-propylamino)-2,4-dioxo-1,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-3-yl]-3-phenylpropionate [ No CAS ]
  • 8
  • [ 123-00-2 ]
  • [ 17201-43-3 ]
  • [ 774-07-2 ]
  • [ 67531-68-4 ]
  • 3-[1-(4-cyano-benzyl)-7-(3-morpholin-4-yl-propylamino)-2,4-dioxo-1,4-dihydro-2<i>H</i>-pyrimido[4,5-<i>d</i>]pyrimidin-3-yl]-benzoic acid ethyl ester [ No CAS ]
  • 10
  • [ 17201-43-3 ]
  • [ 94084-75-0 ]
  • 11
  • [ 51779-32-9 ]
  • [ 17201-43-3 ]
  • [ 66389-80-8 ]
YieldReaction ConditionsOperation in experiment
18.5 g (94%) With sodium hydroxide; In tetrahydrofuran; methanol; water; B) Preparation of N-Boc-p-(aminomethyl)benzonitrile. To a stirring suspension of sodium hydride (4.6 g, 115 mmol, 60% dispersion in oil) in tetrahydrofuran (150 mL) was added 4-(bromomethyl)benzonitrile (20.5 g, 105 mmol). To this mixture was added (slowly via an addition funnel) a solution of di-t-butyl iminodicarboxylate (25 g, 115 mmol). After stirring for 16 hours, the mixture was diluted with diethyl ether (500 mL) and washed twice with water (250 mL). The organic phase was then dried (MgSO4), filtered and concentrated to give 40.2 g of crude solid. The resulting solid (28.3 g, 85 mmol) was then dissolved in tetrahydrofuran (150 mL) and a solution of sodium hydroxide (3.4 g, 85 mmol) in methanol (300 mL) was added. After stirring overnight, the solution was concentrated to about one-half volume and water was added to promote precipitation of the product. The precipitate was filtered and dried in vacuo to give 18.5 g (94%) of a white solid.
18.5 g (94%) With sodium hydroxide; In tetrahydrofuran; methanol; water; B) Preparation of N-Boc-p-(aminomethyl)benzonitrile To a stirring suspension of sodium hydride (4.6 g, 115 mmol, 60% dispersion in oil) in tetrahydrofuran (150 mL) was added 4-(bromomethyl)benzonitrile (20.5 g, 105 mmol). To this mixture was added (slowly via an addition funnel) a solution of di-t-butyl iminodicarboxylate (25 g, 115 mmol). After stirring for 16 hours, the mixture was diluted with diethyl ether (500 mL) and washed twice with water (250 mL). The organic phase was then dried (MgSO4), filtered and concentrated to give 40.2 g of crude solid. The resulting solid (28.3 g, 85 mmol) was then dissolved in tetrahydrofuran (150 mL) and a solution of sodium hydroxide (3.4 g, 85 mmol) in methanol (300 mL) was added. After stirring overnight, the solution was concentrated to about one-half volume and water was added to promote precipitation of the product. The precipitate was filtered and dried in vacuo to give 18.5 g (94%) of a white solid.
18.5 g (94%) With sodium hydroxide; In tetrahydrofuran; methanol; water; B) Preparation of N-Boc-p-(aminomethyl)benzonitrile To a stirring suspension of sodium hydride (4.6 g, 115 mmol, 60% dispersion in oil) in tetrahydrofuran (150 mL) was added 4-(bromomethyl)benzonitrile (20.5 g, 105 mmol). To this mixture was added (slowly via an addition funnel) a solution of di-t-butyl iminodicarboxylate (25 g, 115 mmol). After stirring for 16 hours, the mixture was diluted with diethyl ether (500 mL) and washed twice with water (250 mL). The organic phase was then dried (MgSO4), filtered and concentrated to give 40.2 g of crude solid. The resulting solid (28.3 g, 85 mmol) was then dissolved in tetrahydrofuran (150 mL) and a solution of sodium hydroxide (3.4 g, 85 mmol) in methanol (300 mL) was added. After stirring overnight, the solution was concentrated to about one-half volume and water was added to promote precipitation of the product. The precipitate was filtered and dried in vacuo to give 18.5 g (94%) of a white solid.
  • 12
  • [ 5932-27-4 ]
  • [ 17201-43-3 ]
  • [ 1034188-25-4 ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; In ethanol; at 60℃; for 5h; Description 6; Ethyl i-^-cyanophenylJmethyll-IH-pyrazole-S-carboxylate (D6); Benzyl bromide (12.46 g), ethyl 1 H-pyrazole-3-carboxylate (D1 ) (8.89 g) and potassium te/f-butoxide (8.75 g) were dissolved in EtOH (600 ml) and heated to 60 °C for 5 hours. The reaction mixture was then evaporated to dryness, re-dissolved in H2O and extracted with EtOAc (x 3). The combined organics were washed with brine, dried over MgSO4 and evaporated to dryness. The crude residue was purified on a large Flash 75 cartridge, eluting with a 50 percent mixture of EtOAc in hexane to give the desired isomer and then 75 percent EtOAc in hexane to give the undesired isomer. The former was recrystallized from EtOAc/hexane to give the title compound (5.24 g) as white crystals. deltaH (MeOD, 400MHz): 1.41 (3H, t), 4.42 (2H, q), 5.47 (2H, s), 6.68 (1 H, d), 7.28 (2H, d), 7.43 (1 H, d), 7.64 (2H, d). MS (ES): C14H13N3O2 requires 255.28; found 256 (M+H).
  • 13
  • [ 150008-24-5 ]
  • [ 17201-43-3 ]
  • [ 1229313-19-2 ]
  • 14
  • [ 22300-52-3 ]
  • [ 17201-43-3 ]
  • [ 1248676-26-7 ]
  • [ 1248676-63-2 ]
  • 15
  • [ 93247-78-0 ]
  • [ 17201-43-3 ]
  • [ 1196052-11-5 ]
YieldReaction ConditionsOperation in experiment
75% To a solution of <strong>[93247-78-0]methyl 1H-indole-7-carboxylate</strong> (1 eq.) in DMF (0.29 M) cooled to 0°C was added potassium tert-butoxide (1.2 eq.) such that the reaction temperature does not exceed 5°C. The resulting suspension was stirred at 0°C for 30 mm and then at RT for 30 mm. The solution was re-cooled to 0°C and 4-(bromomethyl)benzonitrile (1.2 eq.) in DMF (0.69M) was added dropwise. The reaction mixture was allowed to warm slowly to RT over 16 h and then quenched with the addition of ice-water and extracted with EtOAc. The combined organic extracts were washed further with water, 10percent aq. NaHCO3 and brine, dried over Mg504, and filtered. Concentration of the filtrate in vacuo furnished the crude reaction product as a yellow viscous oil, which was purified by column chromatography (5i02, gradient elution, 9:1 Hexane/EtOAc to EtOAc) to afford the product as a colorless oil that solidified upon standing (75percent yield).
Production Example 6; To a mixture of <strong>[93247-78-0]methyl 1H-indole-7-carboxylate</strong> (100 mg) and DMF (1 mL) was added potassium tert-butoxide (75 mg) at room temperature, followed by stirring for 5 minutes. To the reaction mixture was added 4-(bromomethyl)benzonitrile (131 mg), followed by stirring at room temperature for 2 hours. Water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate, and then the solvent was evaporated to obtain crude methyl 1-(4-cyanobenzyl)-1H-indole-7-carboxylate (211 mg). To a mixture of crude methyl 1-(4-cyanobenzyl)-1H-indole-7-carboxylate (211 mg), THF (10 mL), and methanol (5 mL) was added a 1 M aqueous sodium hydroxide solution (2.5 mL), and the obtained mixed liquid was stirred at 60°C overnight. After leaving to be cooled to room temperature, the solvent was evaporated under reduced pressure, and to the obtained residue was added ethyl acetate, followed by extraction with water. The aqueous layer was neutralized by adding 1 M hydrochloric acid (2. mL), and extracted with ethyl acetate. This organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated to obtain crude 1-(4-carbamoylbenzyl)-1H-indole-7-carboxylic acid (230 mg). To a mixture of crude 1-(4-carbamoylbenzyl)-1H-indole-7-carboxylic acid (229 mg), methyl (S)-4-[1-aminoethyl]benzoate hydrochloride (123 mg), and HOBt (23 mg) in DMF (3 mL) was added EDCI-HCl (150 muL), followed by stirring at room temperature for 3 hours. Water was added thereto, followed by extraction with ethyl acetate-diethyl ether. The organic layer was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate. After evaporating the solvent, to the obtained residue was added ethanol. The precipitated solid was collected by filtration and dried to obtain methyl (S)-4-[1-([1-(4-carbamoylbenzyl)-1H-indol-7-yl]carbonyl}amino)ethyl]benzoate (142 mg).
  • 16
  • [ 932041-13-9 ]
  • [ 17201-43-3 ]
  • [ 1185287-57-3 ]
YieldReaction ConditionsOperation in experiment
68.8% A suspension of 1.67 g of 60% sodium hydride in 134.0 mL dry DMF was added 7 g <strong>[932041-13-9]methyl 7-fluoro-1H-indazole-3-carboxylate</strong> in 10 mL dry DMF drop wise via syringe at room temperature. The mixture was allowed to stir for approximately 1 h at room temperature and was then added 8.02 g of 4-cyanobenzyl bromide in 56 mL DMF drop wise via syringe. The resulting mixture was then heated to 60 C. and allowed to stir over night. Reaction was allowed to cool to room temperature and was quenched by the careful addition of water (500 mL). The aqueous solution was extracted with ethyl acetate (4×150 mL). The organic solution is washed with brine (2×200 mL), dried (MgSO4), filtered and concentrated to an oil. Crude reaction was purified via MPLC (25%-50% ethyl ether/heptane) to afford 7.68 g (68.8%) of methyl 1-(4-cyanobenzyl)-7-fluoro-1H-indazole-3-carboxylate as a light yellow solid. 1H NMR (400 MHz, CDCl3) delta 8.01 (d, J=8.0 Hz, 1H), 7.60 (d, J=7.8 Hz, 2H), 7.36 (d, J=8.0 Hz, 2H, 7.20-7.28 (m, 1H), 7.06-7.14 (m, 1H), 5.85 (s, 2H), 4.06 (s, 3H). MS (ESI) m/z 310 (M+H)+.
  • 17
  • [ 58966-93-1 ]
  • [ 17201-43-3 ]
  • [ 1313212-18-8 ]
  • 18
  • [ 2296-23-3 ]
  • [ 17201-43-3 ]
  • 4-cyanobenzyl 4-cyano-2-iodophenyl ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% General procedure: Potassium carbonate (1-1.6 equiv) was added to a stirred solution of the phenol (1 equiv) in DMF. After 30 min the cyanobenzyl bromide (1-1.2 equiv) was added, and the mixture was stirred until completion (1-4 days). The reaction mixture was poured over ice or diluted with water. The precipitated product was filtered off and recrystallized if needed.
  • 19
  • [ 1196156-42-9 ]
  • [ 17201-43-3 ]
  • C16H12N4O2 [ No CAS ]
  • methyl 1-(4-cyanobenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate [ No CAS ]
  • 20
  • [ 4214-79-3 ]
  • [ 17201-43-3 ]
  • C13H9ClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With silver carbonate; In tetrahydrofuran; for 16h;Reflux; General procedure for the synthesis of DlTo a stirred mixture of <strong>[4214-79-3]5-chloro-2-hydroxypyridine</strong> (15.0 g, 76.5 mmol) in anhydrous THF (200 mL) were added 4-cyanobenzyl bromide (8.26 g, 63.8 mmol) and Ag2CO3 (10.5 g, 38.3 mmol). The resulting mixture was refluxed for 16 hours. The mixture was cooled to room temperature and filtered. The filter cake was washed with THF (100 mL). The combined filtrate was concentrated under reduced pressure to afford a residue, which was purified by combi flash (PE/EtOAc=92/8 to 70/30) to afford Dl.
  • 21
  • [ 4214-79-3 ]
  • [ 17201-43-3 ]
  • C13H13ClN2O [ No CAS ]
  • 22
  • [ 391-12-8 ]
  • [ 17201-43-3 ]
  • 1-(4-cyanobenzyl)-7-trifluoromethylisatin [ No CAS ]
  • 23
  • [ 391-12-8 ]
  • [ 17201-43-3 ]
  • (S)-1-(4-cyanobenzyl)-3-hydroxy-3-(phenylethynyl)-7-trifluoromethyloxindole [ No CAS ]
  • 24
  • [ 109-11-5 ]
  • [ 17201-43-3 ]
  • 4-[(3-oxomorpholin-4-yl)methyl]benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With potassium carbonate; In acetonitrile; at 85℃; for 19h; A solution of 4-(bromomethyl)benzonitrile (2.0 g, 10.2 mmol), <strong>[109-11-5]morpholin-3-one</strong> (2.5 equiv., 2.1 1 g, 20.9 mmol), and potassium carbonate (2 equiv., 2.82 g, 20.4 mmol) in acetonitrile (4.7 mL) was heated at 85C for 19 hours. After cooling to 25C, the solvent was removed under reduced pressure. The residue obtained was dissolved in ethyl acetate and washed with water. The organic layer was then dried over sodium sulfate, and concentrated under reduced pressure. The crude yellow residue obtained was purified by flash chromatography over silica gel (cyclohexane:EtOAc eluent gradient 9: 1 to 0: 1 ) to give 1.13 g (51 % yield) of the title compound as a yellow oil. LC/MS (Method A) retention time = 0.58 minutes, 217 (M+H). (0556) NMR (400 MHz, CDCI3) δ ppm: 7.65 (d, 2H), 7.38(d, 2H), 4.68 (s, 2H), 4.25 (t, 2H), 3.85 (t, 2H), 3.30 (t, 2H).
1.13 g With potassium carbonate; In acetonitrile; at 85℃; for 19h; A heterogenous solution of 4-(bromomethyl)benzonitrile (2.0 g, 10.2 mmol), <strong>[109-11-5]morpholin-3-one</strong> (2.5 equiv., 2.1 1 g, 20.9 mmol), and potassium carbonate (2 equiv., 2.82 g, 20.4 mmol) in acetonitrile (4.7 mL) was heated at 85C for 19 hours. After cooling to 25C, the solvent was removed under reduced pressure. The residue obtained was dissolved in ethyl acetate, washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The resultant crude yellow obtained was purified by flash chromatography over silica gel (cyclohexane:EtOAc eluent gradient 9:1 to 0:1 ) to give 1.13 g of the title compound as a yellow oil. LC/MS (Method A) retention time = 0.58 minutes, 217 (M+H). (0376) NMR (400 MHz, CDCIs) δ ppm: 7.65 (d, 2H), 7.38 (d, 2H), 4.68 (s, 2H), 4.25 (t, 2H), 3.85 (t, 2H), 3.30 (t, 2H).
  • 25
  • [ 271-34-1 ]
  • [ 17201-43-3 ]
  • 4-((1H-pyrrolo[3,2-c]pyridin-1-yl)methyl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% To a solution of 1H-pyrrolo[3,2-c]pyridine (1.0 g, 8.5 mmol) in DMF (40 mL) under nitrogen at 0C was added NaH (60% in mineral oil, 0.51 g, 12.8 mmol) in portions and after stirring for 15 mm was added 4-(bromomethyl)benzonitrile (2.5 g, 12.8 mmol) in portions. The reaction mixture was stirred at 0 C for 2 h then at room temperature for 1 h and quenched with saturated ammonium chloride solution then diluted with ethyl acetate (100 mL) and water (100 mL). The organic layer was separated, washed with brine (3 x 100 mL), dried (Na2504) and concentrated. The crude product was purified by silica gel column chromatography using methylene chloride:ethyl acetate: methanol (5:3 :2) to afford 4-( 1H-pyrrolo[3 ,2-c]pyridin- 1 -ylmethyl)benzonitrile (1.2 g, 60%) as a solid. ‘HNIVII{ (400 MHz, CDC13): 5.38 (s, 2H), 6.68 (d, 1H, J = 3.2 Hz), 7.11-7.17 (m, 4H), 7.54 (d, 2H, J = 8.0 Hz), 8.27 (d, 1H, J = 5.6 Hz), 8.94 (s, 1H).
  • 26
  • [ 130596-62-2 ]
  • [ 17201-43-3 ]
  • 4-((4,4-dimethyl-1,4-azasilinan-1-yl)methyl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine; In dichloromethane; at 25 - 30℃; To a solution of 4-(bromomethyl)benzonitrile (2 g, 10.2 mmol) in dry DCM (40 mL)were added 4,4-dimethylsilapiperidine hydrochloride (2.01 g, 12.2 mmol), triethyl amine (4.3 mL, 30.6 mmol) and stirred at RT (25 - 30 C) 8-10 h. Water was added and the organic layer was separated, dried over Na2SO4 and concentrated. The crude was purified by column chromatography using 20 - 30 % Ethylacetate: pet ether to give the pure product (1.97 g, 80% yield). ?H NMR (200 MHz, CDC13) oe ppm 7.62 -7.58 (m, 2H), 7.48 - 7.44 (m, 2H), 3.59 (s, 2H), 2.67 (t, J = 6.3 Hz, 4H), 0.76 (t, J =6.3 Hz, 4H), 0.06 (m, 6H); ?3C NMR (50 MHz, CDC13) oe ppm 145.6, 132.0, 129.2,119.1, 110.5, 62.4, 52.7, 13.9, -3.1
  • 27
  • [ 617-05-0 ]
  • [ 17201-43-3 ]
  • ethyl 4-((4-cyanobenzyl)oxy)-3-methoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% In a round bottomed flask equipped with a nitrogen inlet and a magnetic stir bar, potassium carbonate (1.86 g, 13.46 mmol), <strong>[617-05-0]ethyl 4-hydroxy-3-methoxybenzoate</strong> (1.2 g, 6.12 mmol) and CH3CN (26 mL) was added. The mixture was stirred for 30 minutes before 4- (bromomethyl)benzonitrile (1.32 g, 6.73 mmol) was added. The mixture was then stirred at reflux temperature overnight. The reaction mixture was rotary evaporated. Water (100 mL) was then added to the residue and the aqueous was then extracted with EtOAc (3 x 50 mL). The combined organic layers were evaporated and then dried in vacuo yielding 2.04 g (96 %) of ethyl 4-((4-cyanobenzyl)oxy)-3-methoxybenzoate as product. (0332) 1H NMR (400 MHz, Chloroform-d) delta 7.80 - 7.35 (m, 6H), 6.82 (d, J = 8.4 Hz, 1H), 5.24 (s, 2H), 4.34 (q, J = 7.1 Hz, 2H), 3.93 (s, 3H), 1.36 (t, J = 7.1 Hz, 3H).
  • 28
  • [ 17201-43-3 ]
  • [ 82413-63-6 ]
 

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