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

HRID 1432469Notes

Reaction equation

HRID 1432469 reaction equation
[OH:1][C:2]1[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O: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])[O: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 546945694-Hydroxy-5-phenylfuran-2(5H)-one

Product 1

HCID 57933458N-(2-{6-Fluoro-2-[(4-hydroxy-2-oxo-5-phenyl-2,5-dihydro-furan-3-yl)-phenyl-methyl]-1H-indol-3-yl)-ethyl)-acetamide

Procedure

Using general procedure C, 4-hydroxy-5-phenyl-5H-furan-2-one (Lit. 14) 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 brown solid. MS: 485.0 ([M+H]+).

Sources & evidence

ORD record
ord-84760ccd20344a71848fdda31d8b11cc
Source dataset
uspto-grants-2009_11
Patent number
US07612099B2

Reaction notes

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