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

HRID 1432477Notes

Reaction equation

HRID 1432477 reaction equation
[OH:1][C:2]1[CH:6]([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:5][C:4](=[O:16])[CH:3]=1.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F:25][C:26]1[CH:34]=[C:33]2[C:29]([C:30]([CH2:35][CH2:36][NH:37][C:38](=[O:40])[CH3:39])=[CH:31][NH:32]2)=[CH:28][CH:27]=1>>[F:25][C:26]1[CH:34]=[C:33]2[C:29]([C:30]([CH2:35][CH2:36][NH:37][C:38](=[O:40])[CH3:39])=[C:31]([CH:17]([C:3]3[C:4](=[O:16])[O:5][CH:6]([CH2:7][CH2:8][CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:2]=3[OH:1])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[NH:32]2)=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 10751398N-[2-(6-Fluoro-1H-indol-3-yl)-ethyl]-acetamideHCID 690668074-hydroxy-5-(3-phenyl-propyl)-5H-furan-2-one

Product 1

HCID 57933466N-[2-(6-Fluoro-2-{[4-hydroxy-2-oxo-5-(3-phenyl-propyl)-2,5-dihydro-furan-3-yl]-phenyl-methyl}-1H-indol-3-yl)-ethyl]-acetamide

Procedure

Using general procedure C, 4-hydroxy-5-(3-phenyl-propyl)-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: 525.2 ([M−H]−).

Sources & evidence

ORD record
ord-e32cf092ef92429ca13e9584279e8758
Source dataset
uspto-grants-2009_11
Patent number
US07612099B2

Reaction notes

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