Benzaldehyde → N-(2-{6-Fluoro-2-[(4-hydroxy-2-oxo-5-phenethyl-2,5-dihydro-furan-3-yl)-phenyl-methyl]-1H-indol-3-yl}-ethyl)-acetamide

HRID 1432476Notes

Reaction equation

HRID 1432476 reaction equation
[OH:1][C:2]1[CH:6]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5][C:4](=[O:15])[CH:3]=1.[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[F:24][C:25]1[CH:33]=[C:32]2[C:28]([C:29]([CH2:34][CH2:35][NH:36][C:37](=[O:39])[CH3:38])=[CH:30][NH:31]2)=[CH:27][CH:26]=1>>[F:24][C:25]1[CH:33]=[C:32]2[C:28]([C:29]([CH2:34][CH2:35][NH:36][C:37](=[O:39])[CH3:38])=[C:30]([CH:16]([C:3]3[C:4](=[O:15])[O:5][CH:6]([CH2:7][CH2:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[C:2]=3[OH:1])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:31]2)=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 10751398N-[2-(6-Fluoro-1H-indol-3-yl)-ethyl]-acetamideHCID 690690364-hydroxy-5-phenethyl-5H-furan-2-one

Product 1

HCID 57933412N-(2-{6-Fluoro-2-[(4-hydroxy-2-oxo-5-phenethyl-2,5-dihydro-furan-3-yl)-phenyl-methyl]-1H-indol-3-yl}-ethyl)-acetamide

Procedure

Using general procedure C, 4-hydroxy-5-phenethyl-5H-furan-2-one (Lit. 13) was reacted with benzaldehyde and N-[2-(6-fluoro-1H-indol-3-yl)-ethyl]-acetamide (Example 18.1.) to give the title compound as pale red solid. MS: 511.1 ([M−H]−).

Sources & evidence

ORD record
ord-6c978e8a46664042956d953760115196
Source dataset
uspto-grants-2009_11
Patent number
US07612099B2

Reaction notes

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