Diisopropylethylamine → N-(2-(6-Chloro-5-methyl-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)benzamide

HRID 1777678Notes

Reaction equation

HRID 1777678 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][CH2:12][NH2:13])=[CH:7][NH:8]2)=[CH:4][C:3]=1[CH3:14].[F:15][C:16]1[CH:17]=[C:18]([CH:29]=[CH:30][CH:31]=1)[CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=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:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][CH2:12][NH:13][C:24](=[O:25])[C:23]3[CH:22]=[CH:21][C:20]([CH2:19][C:18]4[CH:29]=[CH:30][CH:31]=[C:16]([F:15])[CH:17]=4)=[CH:28][CH:27]=3)=[CH:7][NH:8]2)=[CH:4][C:3]=1[CH3:14]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668321552-(6-chloro-5-methyl-1H-indol-3-yl)ethanamineHCID 679746154-(3-Fluoro-benzyl)-benzoic acid

Product 1

HCID 67974633N-(2-(6-Chloro-5-methyl-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)benzamideYield 14.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-(6-Chloro-5-methyl-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)benzamide was prepared according to Method A starting from 2-(6-chloro-5-methyl-1H-indol-3-yl)ethanamine (0.172 g; 0.825 mmol), 4-(3-fluorobenzyl)benzoic acid (0.190 g, 0.825 mmol), HATU (0.313 g; 0.825 mmol) and N,N-diisopropylethylamine (0.355 mL; 2.06 mmol) in DMF (5 mL). The crude material was purified by preparative HPLC (method 2) to afford 0.049 g (14%) of the title compound as a white solid.

Workup

  1. customN-(2-(6-Chloro-5-methyl-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)benzamide was prepared
  2. customThe crude material was purified by preparative HPLC (method 2)

Sources & evidence

ORD record
ord-9fb0b3c713f74034b7db984e0595b678
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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