Cyclopentanone → HCID 68524505, compound

HRID 2263485Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=[O:11].[C:13]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14]1.[OH-].[Na+]>>[C:13]1([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]=2[C:10]([OH:12])=[O:11])[CH2:17][CH2:16][CH2:15][CH:14]=1

Participants

Reactant 3

HCID 8452Cyclopentanone

HCID 14798Sodium Hydroxide

HCID 72899Indole-2-carboxylic acid

Product 1

HCID 68524505HCID 68524505, compound

Procedure

Condensation of the indole carboxylic acid with cyclopentanone in the presence of aqueous sodium hydroxide gave the 3-cyclopentenyl indole carboxylic acid, which was subjected to hydrogenation in the presence of catalytic amount of palladium on carbon to afford the corresponding cyclopentyl carboxylic acid in 80% overall yield. Double methylation of the carboxylic acid and the nitrogen with methyl carbonate in NMP at 130° C. provided the N-methyl indole carboxylate methyl ester in 90% yield. Bromination of the indole carboxylate with bromine in acetonitrile furnished the 2-bromo-3-cyclopentyl indole carboxylate in 90% yield.

Sources & evidence

ORD record: ord-87d511a35c2842ccb992e402116e4c6c
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851625B2

Reaction notes

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