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

HRID 1432455Notes

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.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH2:32][CH2:33][NH:34][C:35](=[O:37])[CH3:36])=[CH:24]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:24]2[NH:23][C:31]3[C:26]([C:25]=2[CH2:32][CH2:33][NH:34][C:35](=[O:37])[CH3:36])=[CH:27][CH:28]=[CH:29][CH:30]=3)=[C:9]1[OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 70547N-Acetyltryptamine

HCID 690635555-benzyl-4-hydroxy-5H-furan-2-one

Product 1

HCID 57933422N-(2-{2-[(5-Benzyl-4-hydroxy-2-oxo-2,5-dihydro-furan-3-yl)-phenyl-methyl]-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-(1H-indol-3-yl)-ethyl]-acetamide to give the title compound as a white solid. MS: 481.0 ([M+H]+).

Sources & evidence

ORD record: ord-6ad59312235c4e479d8852c90c09c7f1
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612099B2

Reaction notes

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