3-Chloro-1H-indole-6-carboxylic acid → 3-Chloro-N-[(R)-1-phenyl-2-[3-(piperidin-1-yl)propoxy]-ethyl]-1H-indole-6-carboxamide

HRID 32452Notes

Reaction equation

HRID 32452 reaction equation
[C:1]1([C@@H:7]([NH2:19])[CH2:8][O:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:20][C:21]1[C:29]2[C:24](=[CH:25][C:26]([C:30](O)=[O:31])=[CH:27][CH:28]=2)[NH:23][CH:22]=1>>[Cl:20][C:21]1[C:29]2[C:24](=[CH:25][C:26]([C:30]([NH:19][C@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][O:9][CH2:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)=[O:31])=[CH:27][CH:28]=2)[NH:23][CH:22]=1

Participants

3

Reactant 2

HCID 155430423-Chloro-1H-indole-6-carboxylic acidHCID 69307910(R)-1-phenyl-2-[3-(piperidin-1-yl)propoxy]ethylamine

Product 1

HCID 693132163-Chloro-N-[(R)-1-phenyl-2-[3-(piperidin-1-yl)propoxy]-ethyl]-1H-indole-6-carboxamide

Procedure

Using coupling method A, (R)-1-phenyl-2-[3-(piperidin-1-yl)propoxy]ethylamine (218 mg, 0.83 mmol) and 3-chloro-indole-6-carboxylic acid (179 mg, 0.91 mmol) afforded, after purification (SiO2: 50% EtOAc in hexane), 115 mg (32%) of the title compound.

Workup

  1. customafforded
  2. customafter purification (SiO2: 50% EtOAc in hexane), 115 mg (32%) of the title compound

Sources & evidence

ORD record
ord-047ba596d8bd4a82b112b732fbbde452
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

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