Benzaldehyde → 3-[(5-Fluoro-3-methyl-1h-indol-2-yl)-phenyl-methyl]-4-hydroxy-5,5-dimethyl-1,5-dihydro-pyrrol-2-one

HRID 1432496Notes

Reaction equation

[OH:1][C:2]1[C:6]([CH3:8])([CH3:7])[NH:5][C:4](=[O:9])[CH:3]=1.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[F:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2[CH3:28]>>[F:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]([CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]1[C:4](=[O:9])[NH:5][C:6]([CH3:8])([CH3:7])[C:2]=1[OH:1])=[C:22]2[CH3:28]

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 223515035-Fluoro-3-methyl-1H-indole

HCID 667254294-hydroxy-5,5-dimethyl-1,5-dihydro-2H-pyrrol-2-one

Product 1

HCID 579334383-[(5-Fluoro-3-methyl-1h-indol-2-yl)-phenyl-methyl]-4-hydroxy-5,5-dimethyl-1,5-dihydro-pyrrol-2-one

Procedure

Using general procedure D, rac-4-hydroxy-5,5-dimethyl-1,5-dihydro-pyrrol-2-one (Lit. 18) was reacted with benzaldehyde and 5-fluoro-3-methyl-1H-indole to give the title compound as a yellow solid. MS: 365.1 ([M+H]+).

Sources & evidence

ORD record: ord-2873d50e40164cbf97480dfbd76a51b9
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612099B2

Reaction notes

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