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

HRID 32404Notes

Reaction equation

HRID 32404 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][CH:21]=[CH:20][C:19]=2[F:24])[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][CH:21]=[CH:20][C:19]=2[F:24])[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 693080934-[2-Amino-2-(2-fluorophenyl)-ethoxymethyl]piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 693107064-{2-[(3-Chloro-1H-indole-6-carbonyl)amino]-2-(2-fluoro-phenyl)ethoxymethyl}piperidine-1-carboxylic acid tert-butyl ester

Procedure

Using coupling method A, 4-[2-amino-2-(2-fluorophenyl)-ethoxymethyl]piperidine-1-carboxylic acid tert-butyl ester (600 mg, 1.7 mmol) and 3-chloroindole-6-carboxylic acid (367 mg, 1.9 mmol) afforded, after purification (SiO2: 10 DCM: 2 EtOAc: 2 Hexane: 0 to 0.125 isopropyl amine), 800 mg (90%) of the title compound.

Workup

  1. customafforded
  2. customafter purification (SiO2: 10 DCM: 2 EtOAc: 2 Hexane: 0 to 0.125 isopropyl amine), 800 mg (90%) of the title compound

Sources & evidence

ORD record
ord-c3961626a6114b3389352f312c3bfa2a
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

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