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

HRID 1432505Notes

Reaction equation

HRID 1432505 reaction equation
[OH:1][C:2]1[C@@:6]([CH3:13])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:5][C:4](=[O:14])[CH:3]=1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[F:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][CH:28]=[C:27]2[CH3:33]>>[F:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28]([CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]1[C:4](=[O:14])[NH:5][C@:6]([CH3:13])([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:2]=1[OH:1])=[C:27]2[CH3:33]

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 223515035-Fluoro-3-methyl-1H-indoleHCID 69071890(R)-4-hydroxy-5-methyl-5-phenyl-1,5-dihydro-pyrrol-2-one

Product 1

HCID 57933413(R)-3-[(5-Fluoro-3-methyl-1H-indol-2-yl)-phenyl-methyl]-4-hydroxy-5-methyl-5-phenyl-1,5-dihydro-pyrrol-2-one

Procedure

Using general procedure D, (R)-4-hydroxy-5-methyl-5-phenyl-1,5-dihydro-pyrrol-2-one (prepared according to Lit. 11, see also Lit. 19) was reacted with benzaldehyde and 5-fluoro-3-methyl-1H-indole to give the title compound as a pale yellow foam. MS: 425.4 ([M−H]−).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-dd5f810426d849fc833a2ed06f8244c1
Source dataset
uspto-grants-2009_11
Patent number
US07612099B2

Reaction notes

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