5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid → N-[4-Methoxy-6-(pyrrolidin-1-yl)pyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide

HRID 506508Notes

Reaction equation

HRID 506508 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:6]([C:19](O)=[O:20])=[CH:5]2.[CH3:22][O:23][C:24]1[C:29]([NH2:30])=[CH:28][N:27]=[C:26]([N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[CH:25]=1>>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([N:31]2[CH2:32][CH2:33][CH2:34][CH2:35]2)[N:27]=[CH:28][C:29]=1[NH:30][C:19]([C:6]1[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)=[O:20]

Participants

3

Reactant 2

HCID 574315135-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acidHCID 574315194-Methoxy-2-(pyrrolidin-1-yl)-5-aminopyridine

Product 1

HCID 57431495N-[4-Methoxy-6-(pyrrolidin-1-yl)pyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamideYield 73.3%

Procedure

The process is carried out according to the method described in example 2, using 0.5 g (1.74 mmol) of 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid (example 1.1) and 0.424 g (2.09 mmol) of 4-methoxy-2-(pyrrolidin-1-yl)-5-aminopyridine, obtained in step 6.1 (Compound Vb). 0.59 g of the expected product is thus isolated.

Workup

  1. customobtained in step 6.1 (Compound Vb)

Sources & evidence

ORD record
ord-bf2e853da2b94c1cba84d2fd665c883d
Source dataset
uspto-grants-2010_08
Patent number
US07786104B2

Reaction notes

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