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

HRID 506512Notes

Reaction equation

HRID 506512 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]([OH:21])=O)=[CH:5]2.[CH3:22][C:23]1[C:28]([NH2:29])=[CH:27][CH:26]=[C:25]([N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:24]=1>>[CH3:22][C:23]1[C:28]([NH:29][C:19]([C:6]2[N:7]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)[C:8]3[C:4]([CH:5]=2)=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)=[O:21])=[CH:27][CH:26]=[C:25]([N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:24]=1

Participants

3

Reactant 2

HCID 574315135-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acidHCID 574315232-Methyl-6-(pyrrolidin-1-yl)pyridin-3-amine

Product 1

HCID 57431521N-[2-Methyl-6-(pyrrolidin-1-yl)pyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamideYield 48.3%

Procedure

The process is carried out according to the method described in example 5.3, using 0.4 g (1.39 mmol) of 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid (example 1.1) and 0.32 g (1.81 mmol) of 2-methyl-6-(pyrrolidin-1-yl)-3-aminopyridine (compound no. Vd), described in step 9.2. 0.3 g of the expected product is thus isolated.

Sources & evidence

ORD record
ord-7d1137c63c794c368b0040bac7bd429e
Source dataset
uspto-grants-2010_08
Patent number
US07786104B2

Reaction notes

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