5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid → N-[6-(3-Azabicyclo[3.1.0]hex-3-yl)pyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide

HRID 506522Notes

Reaction equation

HRID 506522 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.[CH:22]12[CH2:27][CH:26]1[CH2:25][N:24]([C:28]1[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][N:29]=1)[CH2:23]2>>[CH:26]12[CH2:27][CH:22]1[CH2:23][N:24]([C:28]1[N:29]=[CH:30][C:31]([NH:34][C:19]([C:6]3[N:7]([CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=4)[C:8]4[C:4]([CH:5]=3)=[CH:3][C:2]([F:1])=[CH:10][CH:9]=4)=[O:21])=[CH:32][CH:33]=1)[CH2:25]2

Participants

3

Reactant 2

HCID 574315135-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acidHCID 574315312-(3-Azabicyclo[3.1.0]hex-3-yl)-5-aminopyridine

Product 1

HCID 57431499N-[6-(3-Azabicyclo[3.1.0]hex-3-yl)pyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamideYield 73.6%

Procedure

The process is carried out according to the method described in example 2, using 0.15 g (0.52 mmol) of 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid and 0.1 g (0.57 mmol) of 2-(3-azabicyclo[3.1.0]hex-3-yl)-5-aminopyridine, prepared in step 12.2. 0.17 g of the expected product is thus isolated.

Workup

  1. customprepared in step 12.2

Sources & evidence

ORD record
ord-140bb54e98004ac880061fb8729abe2f
Source dataset
uspto-grants-2010_08
Patent number
US07786104B2

Reaction notes

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