HCID 18505436, compound → HCID 18505433, compound

HRID 1357100Notes

Reaction equation

HRID 1357100 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[C:14]([N:16]([CH3:32])[C:17](=[O:31])[C:18]=1[C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]([CH3:30])[CH:20]=1)=[O:15]>CN(C=O)C.[C].[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[CH:13]1[CH:18]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=3)[N:21]([CH3:30])[CH:20]=2)[C:17](=[O:31])[N:16]([CH3:32])[C:14]1=[O:15]

Participants

4

Reactant 1

HCID 18505436HCID 18505436, compound

Product 1

HCID 18505433HCID 18505433, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,3-bis(5-methoxy-1-methyl-1H-indol-3-yl)-N-methylmaleimide (70 mg, 0.16 mmol) in DMF (2 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 3,4-bis(5-methoxy-1-methyl-1H-indol-3-yl)-1-methyl-2,5-dioxopyrrolidine (42 mg, 60.4%) as pale red solids.

Workup

  1. customThe palladium-carbon was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography over silica gel (ethyl acetate:n-hexane=2:1)

Sources & evidence

ORD record
ord-fcff4053694d4b50a56eb9b914555997
Source dataset
uspto-grants-2003_07
Patent number
US06589977B1

Reaction notes

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