3-Chloro-1H-indole-6-carboxylic acid → 4-{2-[(3-chloro-1H-indole-6-carbonyl)amino]-2-(4-fluorophenyl)ethoxymethyl}piperidine-1-carboxylic acid tert-butyl ester

HRID 32406Notes

Reaction equation

HRID 32406 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][CH2:16][CH:17]([NH2:25])[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:26][C:27]1[C:35]2[C:30](=[CH:31][C:32]([C:36](O)=[O:37])=[CH:33][CH:34]=2)[NH:29][CH:28]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][O:15][CH2:16][CH:17]([NH:25][C:36]([C:32]2[CH:31]=[C:30]3[C:35]([C:27]([Cl:26])=[CH:28][NH:29]3)=[CH:34][CH:33]=2)=[O:37])[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 155430423-Chloro-1H-indole-6-carboxylic acidHCID 693079574-[2-Amino-2-(4-fluorophenyl)-ethoxymethyl]piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 693079464-{2-[(3-chloro-1H-indole-6-carbonyl)amino]-2-(4-fluorophenyl)ethoxymethyl}piperidine-1-carboxylic acid tert-butyl esterYield 100.6%

Procedure

Using coupling method A, 4-[2-amino-2-(4-fluorophenyl)-ethoxymethyl]piperidine-1-carboxylic acid tert-butyl ester (1.1 g, 3.0 mmol) and 3-chloroindole-6-carboxylic acid (653 mg, 3.3 mmol) afforded 1.6 g (100%) of the title compound as a crude residue, which was used without further purification.

Sources & evidence

ORD record
ord-84c5bf9352fc41ddb9d7695d63b711b7
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

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