2-(1,5-dimethyl-1H-indol-3-yl)-3-(5-methyl-1H-indol-3-yl)-N-methylmaleimide → 3-(1,5-dimethyl-1H-indol-3-yl)-4-(5-methyl-1H-indol-3-yl)-1-methyl-2,5-dioxopyrrolidine
Reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[C:4]([C:12]2[C:13]([N:15]([CH3:29])[C:16](=[O:28])[C:17]=2[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([CH3:27])[CH:25]=3)[NH:20][CH:19]=2)=[O:14])=[CH:3]1>CN(C=O)C.[C].[Pd]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[C:4]([CH:12]2[CH:17]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([CH3:27])[CH:25]=4)[NH:20][CH:19]=3)[C:16](=[O:28])[N:15]([CH3:29])[C:13]2=[O:14])=[CH:3]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 2-(1,5-dimethyl-1H-indol-3-yl)-3-(5-methyl-1H-indol-3-yl)-N-methylmaleimide (100 mg, 0.26 mmol) in DMF (5 mL) was added a small amount of 10% palladium-carbon, and the whole was stirred at room temperature for 1 day under hydrogen atmosphere. The palladium-carbon was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography over silica gel (ethyl acetate:n-hexane =2:1) to obtain 3-(1,5-dimethyl-1H-indol-3-yl)-4-(5-methyl-1H-indol-3-yl)-1-methyl-2,5-dioxopyrrolidine (71 mg, 70.2%) as pale red solids.
Workup
- customThe palladium-carbon was removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by column chromatography over silica gel (ethyl acetate:n-hexane =2:1)
Sources & evidence
- ORD record
- ord-50ea68ec380d45d28fc2870ee068211e
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06589977B1
Reaction notes
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