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

HRID 1432459Notes

Reaction equation

HRID 1432459 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.[CH3:15][CH:16]([CH3:19])[CH:17]=O.[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH2:29][CH2:30][NH:31][C:32](=[O:34])[CH3:33])=[CH:21]1>>[CH2:1]([CH:8]1[O:12][C:11](=[O:13])[C:10]([CH:17]([C:21]2[NH:20][C:28]3[C:23]([C:22]=2[CH2:29][CH2:30][NH:31][C:32](=[O:34])[CH3:33])=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:16]([CH3:19])[CH3:15])=[C:9]1[OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6561IsobutyraldehydeHCID 70547N-AcetyltryptamineHCID 690635555-benzyl-4-hydroxy-5H-furan-2-one

Product 1

HCID 57933453N-(2-{2-[1-(5-Benzyl-4-hydroxy-2-oxo-2,5-dihydro-furan-3-yl)-2-methyl-propyl]-1H-indol-3-yl}-ethyl)-acetamide

Procedure

Using general procedure C, 5-benzyl-4-hydroxy-5H-furan-2-one (Lit. 13) was reacted with 2-methyl-propionaldehyde and N-[2-(1H-indol-3-yl)-ethyl]-acetamide) to give the title compound as a yellow solid. MS: 445.1 ([M−H]−).

Sources & evidence

ORD record
ord-453a3908d3dd4f30a72463a9d9015cbe
Source dataset
uspto-grants-2009_11
Patent number
US07612099B2

Reaction notes

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