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

HRID 1432485Notes

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.[CH2:22]([C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][CH:28]=[C:27]2[CH2:33][CH2:34][NH:35][C:36](=[O:38])[CH3:37])[CH3:23]>>[CH2:22]([C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28]([CH:14]([C:3]1[C:4](=[O:13])[CH2:5][CH:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:2]=1[OH:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[C:27]2[CH2:33][CH2:34][NH:35][C:36](=[O:38])[CH3:37])[CH3:23]

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 45095775N-[2-(5-Ethyl-1H-indol-3-yl)ethyl]acetamide

HCID 690696643-Hydroxy-4-phenyl-cyclopent-2-enone

Product 1

HCID 57933448N-(2-{5-Ethyl-2-[(2-hydroxy-5-oxo-3-phenyl-cyclopent-1-enyl)-phenyl-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-ethyl-1H-indol-3-yl)-ethyl]-acetamide (Lit. 6) to give the title compound as an orange solid. MS: 493.4 ([M+H]+).

Sources & evidence

ORD record: ord-ad6dc6eb77154f9da91cac3d541910ad
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612099B2

Reaction notes

Loading…