o-Phenylbenzoic acid → HCID 67976867, compound

HRID 925336Notes

Reaction equation

HRID 925336 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH2:14].[C:15]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]([C:21](O)=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH:14][C:21]([C:16]1[C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:22]

Participants

6

Reactant 4

HCID 70357o-Phenylbenzoic acidHCID 81531DiisopropylethylamineHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 67976867HCID 67976867, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-(5-chloro-1H-Indol-3-yl)ethyl)biphenyl-2-carboxamide was prepared following Method A starting from 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.100 g; 0.424 mmol), biphenyl-2-carboxylic acid (0.0943 g; 0.466 mmol), HATU (0.193 g; 0.508 mmol) and N,N-diisopropylethylamine (0.179 mL; 1.06 mmol) in DMF (5 mL). Flash chromatography on silica gel (eluent 1 to 10% ethyl acetate in dichloromethane) furnished 0.109 g (68%) of N-(2-(5-chloro-1H-Indol-3-yl)ethyl)biphenyl-2-carboxamide as a white solid.

Workup

  1. customN-(2-(5-chloro-1H-Indol-3-yl)ethyl)biphenyl-2-carboxamide was prepared

Sources & evidence

ORD record
ord-35209b98e8ee4c3889c2cfcac98173fb
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

Loading…