o-Benzylbenzoic acid → HCID 67974911, compound

HRID 1777589Notes

Reaction equation

HRID 1777589 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].[CH2:15]([C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](O)=[O:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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.ClCCl.CO>[CH2:15]([C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([NH:14][CH2:13][CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([Cl:2])[CH:4]=2)[NH:8][CH:7]=1)=[O:25])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 11924o-Benzylbenzoic 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 67974911HCID 67974911, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-Benzyl-N-(2-(5-chloro-1H-indol-3-yl)ethyl)benzamide was prepared following Method A starting from 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.100 g; 0.424 mmol), 2-benzylbenzoic acid (0.102 g; 0.466 mmol), HATU (0.177 g; 0.466 mmol) and N,N-diisopropylethylamine (0.179 mL; 1.06 mmol) in DMF (5 mL). Flash chromatography on silica gel eluting with 1 to 10% methanol in dichloromethane furnished 0.065 g (40%) of 2-benzyl-N-(2-(5-chloro-1H-indol-3-yl)ethyl)benzamide as a white solid.

Workup

  1. custom2-Benzyl-N-(2-(5-chloro-1H-indol-3-yl)ethyl)benzamide was prepared

Sources & evidence

ORD record
ord-f9570d4af26647da99bd3997938a4fd1
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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