Benzaldehyde → N-(2-{2-[(2-Hydroxy-5-oxo-3-phenyl-cyclopent-1-enyl)-phenyl-methyl]-5-methyl-1H-indol-3-yl}-ethyl)-acetamide

HRID 1432487Notes

Reaction equation

HRID 1432487 reaction equation
[OH:1][C:2]1[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][C:4](=[O:13])[CH:3]=1.[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][CH:27]=[C:26]2[CH2:32][CH2:33][NH:34][C:35](=[O:37])[CH3:36]>>[OH:1][C:2]1[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][C:4](=[O:13])[C:3]=1[CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:27]1[NH:28][C:29]2[C:25]([C:26]=1[CH2:32][CH2:33][NH:34][C:35](=[O:37])[CH3:36])=[CH:24][C:23]([CH3:22])=[CH:31][CH:30]=2

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 699129N-[2-(5-methyl-1H-indol-3-yl)ethyl]acetamideHCID 690696643-Hydroxy-4-phenyl-cyclopent-2-enone

Product 1

HCID 57933433N-(2-{2-[(2-Hydroxy-5-oxo-3-phenyl-cyclopent-1-enyl)-phenyl-methyl]-5-methyl-1H-indol-3-yl}-ethyl)-acetamide

Procedure

Using general procedure C, 3-hydroxy-4-phenyl-cyclopent-2-enone (Lit. 17) was reacted with benzaldehyde and N-[2-(5-methyl-1H-indol-3-yl)-ethyl]-acetamide (Lit. 7) to give the title compound as orange solid. MS: 479.0 ([M+H]+).

Sources & evidence

ORD record
ord-2791d43853664028b10ddeb493a6b40a
Source dataset
uspto-grants-2009_11
Patent number
US07612099B2

Reaction notes

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