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

HRID 1432457Notes

Reaction equation

HRID 1432457 reaction equation
[CH2:1]([CH:8]1[O:12][C:11](=[O:13])[CH:10]=[C:9]1[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[F:23][C:24]1[CH:32]=[C:31]2[C:27]([C:28]([CH2:33][CH2:34][NH:35][C:36](=[O:38])[CH3:37])=[CH:29][NH:30]2)=[CH:26][CH:25]=1>>[CH2:1]([CH:8]1[O:12][C:11](=[O:13])[C:10]([CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:29]2[NH:30][C:31]3[C:27]([C:28]=2[CH2:33][CH2:34][NH:35][C:36](=[O:38])[CH3:37])=[CH:26][CH:25]=[C:24]([F:23])[CH:32]=3)=[C:9]1[OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 10751398N-[2-(6-Fluoro-1H-indol-3-yl)-ethyl]-acetamideHCID 690635555-benzyl-4-hydroxy-5H-furan-2-one

Product 1

HCID 57933426N-(2-{2-[(5-benzyl-4-hydroxy-2-oxo-2,5-dihydro-furan-3-yl)-phenyl-methyl]-6-fluoro-1H-indol-3-yl}-ethyl)-acetamide

Procedure

Using general procedure C, 5-benzyl-4-hydroxy-5H-furan-2-one (Lit. 13) was reacted with benzaldehyde and N-[2-(6-fluoro-1H-indol-3-yl)-ethyl]-acetamide to give N-(2-{2-[(5-benzyl-4-hydroxy-2-oxo-2,5-dihydro-furan-3-yl)-phenyl-methyl]-6-fluoro-1H-indol-3-yl}-ethyl)-acetamide as a white solid. MS: 497.4 ([M−H]−).

Sources & evidence

ORD record
ord-930bb5a6b43748eebbdbfacf5cdc01ec
Source dataset
uspto-grants-2009_11
Patent number
US07612099B2

Reaction notes

Loading…