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

HRID 1432482Notes

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.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=O)[CH:15]=1.[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH2:31][CH2:32][NH:33][C:34](=[O:36])[CH3:35])=[CH:23]1>>[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:20]([C:16]1[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=1)[C:23]1[NH:22][C:30]2[C:25]([C:24]=1[CH2:31][CH2:32][NH:33][C:34](=[O:36])[CH3:35])=[CH:26][CH:27]=[CH:28][CH:29]=2

Participants

Reactant 3

HCID 103713-Pyridinecarboxaldehyde

HCID 70547N-Acetyltryptamine

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

Product 1

HCID 57933465N-(2-{2-[(2-Hydroxy-5-oxo-3-phenyl-cyclopent-1-enyl)-pyridin-3-yl-methyl]-1H-indol-3-yl}-ethyl)-acetamide

Procedure

Using general procedure C, 3-hydroxy-4-phenyl-cyclopent-2-enone (Lit. 17) was reacted with pyridine-3-carbaldehyde and N-[2-(1H-indol-3-yl)-ethyl]-acetamide to give the title compound as pale brown solid. MS: 466.3 ([M+H]+).

Sources & evidence

ORD record: ord-5f571b2837214dc79e50c3a605b2792f
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612099B2

Reaction notes

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