Benzaldehyde → N-(2-{6-Fluoro-2-[(2-hydroxy-5-oxo-3-phenyl-cyclopent-1-enyl)-phenyl-methyl]-1H-indol-3-yl}-ethyl)-acetamide

HRID 1432480Notes

Reaction equation

HRID 1432480 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.[F:22][C:23]1[CH:31]=[C:30]2[C:26]([C:27]([CH2:32][CH2:33][NH:34][C:35](=[O:37])[CH3:36])=[CH:28][NH:29]2)=[CH:25][CH:24]=1>>[F:22][C:23]1[CH:31]=[C:30]2[C:26]([C:27]([CH2:32][CH2:33][NH:34][C:35](=[O:37])[CH3:36])=[C:28]([CH:14]([C:3]3[C:4](=[O:13])[CH2:5][CH:6]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:2]=3[OH:1])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:29]2)=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 10751398N-[2-(6-Fluoro-1H-indol-3-yl)-ethyl]-acetamideHCID 690696643-Hydroxy-4-phenyl-cyclopent-2-enone

Product 1

HCID 57933474N-(2-{6-Fluoro-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-(6-fluoro-1H-indol-3-yl)-ethyl]-acetamide (Example 18.1.) to give the title compound as a pink solid. MS: 483.5 ([M+H]+).

Sources & evidence

ORD record
ord-36dea28d0ae24a2d82cfb32f4808eb6d
Source dataset
uspto-grants-2009_11
Patent number
US07612099B2

Reaction notes

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