HCID 15132373, compound → HCID 18505447, compound

HRID 1357099Notes

Reaction equation

HRID 1357099 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12]1[C:13]([N:15]([CH3:30])[C:16](=[O:29])[C:17]=1[C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=2)[NH:20][CH:19]=1)=[O:14]>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)[NH:8][CH:7]=[C:6]2[CH:12]1[CH:17]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=3)[NH:20][CH:19]=2)[C:16](=[O:29])[N:15]([CH3:30])[C:13]1=[O:14]

Participants

4

Reactant 1

HCID 15132373HCID 15132373, compound

Product 1

HCID 18505447HCID 18505447, compoundYield 19.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,3-bis(5-methoxy-1H-indol-3-yl)-N-methylmaleimide (100 mg, 0.25 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 3,4-bis(5-methoxy-1H-indol-3-yl)-1-methyl-2,5-dioxopyrrolidine (20 mg, 19.9%) as a mixture of two isomers (A:B=2:1) 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-1c0f0b23f94c4fb78db2bfaf29219861
Source dataset
uspto-grants-2003_07
Patent number
US06589977B1

Reaction notes

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