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

HRID 2041943Notes

Reaction equation

HRID 2041943 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.[OH:22][CH:23]1[CH2:26][N:25]([C:27]2[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][N:28]=2)[CH2:24]1>>[OH:22][CH:23]1[CH2:26][N:25]([C:27]2[N:28]=[CH:29][C:30]([NH:33][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:31][CH:32]=2)[CH2:24]1

Participants

3

Reactant 2

HCID 574315135-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acidHCID 574315251-(5-Aminopyridin-2-yl)azetidin-3-ol

Product 1

HCID 57431524N-[6-(3-Hydroxyazetidin-1-yl)pyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide

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 0.35 g (2.09 mmol) of 2-(3-hydroxyazetidin-1-yl)-5-aminopyridine, obtained in step 10.2 (Compound Ve).

Workup

  1. customobtained in step 10.2 (Compound Ve)

Sources & evidence

ORD record
ord-320096c8d5934cf99de11bdee57e6ec2
Source dataset
uspto-grants-2013_11
Patent number
US08586573B2

Reaction notes

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