Sodium Iodide → HCID 86699436, compound

HRID 1777664Notes

Reaction equation

HRID 1777664 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.[F:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[C:28]([F:30])[CH:29]=1.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:26]2[CH:25]=[C:24]([F:23])[CH:29]=[C:28]([F:30])[CH:27]=2)=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 86699388N-((5-chloro-1H-indol-3-yl)methyl)-4-(chloromethyl)benzamide

Product 1

HCID 86699436HCID 86699436, compoundYield 15.2%

Reagents, catalysts & solvents 3

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

Procedure

N-((5-Chloro-1H-indol-3-yl)methyl)-4-(3,5-difluorobenzyl)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), 3,5-difluorophenylboronic acid (0.041 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 0.015 g (15%) of the title compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-a8860d3e981047c2adb4c0bab7bd268e
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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