Sodium Iodide → N-((5-Chloro-1H-indol-3-yl)methyl)-4-(3-cyanobenzyl)benzamide

HRID 1777663Notes

Reaction equation

HRID 1777663 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][NH:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20]Cl)=[CH:16][CH:15]=1.[C:23]([C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)#[N:24].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(COC)OC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][NH:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([C:23]#[N:24])[CH:30]=2)=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 86699388N-((5-chloro-1H-indol-3-yl)methyl)-4-(chloromethyl)benzamide

Product 1

HCID 86699435N-((5-Chloro-1H-indol-3-yl)methyl)-4-(3-cyanobenzyl)benzamideYield 30.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

N-((5-Chloro-1H-indol-3-yl)methyl)-4-(3-cyanobenzyl)benzamide was prepared following method B starting from N-((5-Chloro-1H-indol-3-yl)methyl)-4-(chloromethyl)benzamide (0.080 g, 0.240 mmol), 3-cyanophenylboronic acid (0.038 g; 0.252 mmol); Tetrakis(triphenylphosphine)palladium(0) (0.014 g; 0.012 mmol), sodium carbonate (0.051 g; 0.480 mmol) and sodium iodide (0.109 g; 0.720 mmol), in dimethoxyethane (3 mL) and water (1 mL), irradiated in a microwave oven at 130° C. for 15 minutes. Flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in dichloromethane) furnished 0.029 g (30%) of the title compound as a white solid.

Workup

  1. customN-((5-Chloro-1H-indol-3-yl)methyl)-4-(3-cyanobenzyl)benzamide was prepared

Sources & evidence

ORD record
ord-7b75ab6a85a647ceaf707bcf0aa6e381
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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