HCID 9951207, compound → HCID 18505437, compound

HRID 1357101Notes

Reaction equation

HRID 1357101 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[CH:15]=3)[NH:10][CH:9]=2)=[C:4]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([CH3:27])[CH:25]=3)[NH:20][CH:19]=2)[C:3]1=[O:28]>CN(C=O)C.[C].[Pd]>[CH3:1][N:2]1[C:3](=[O:28])[CH:4]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([CH3:27])[CH:25]=3)[NH:20][CH:19]=2)[CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[CH:15]=3)[NH:10][CH:9]=2)[C:6]1=[O:7]

Participants

4

Reactant 1

HCID 9951207HCID 9951207, compound

Product 1

HCID 18505437HCID 18505437, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-methyl-2,3-bis(5-methyl-1H-indol-3-yl)maleimide (150 mg, 0.41 mmol) in DMF (3 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 1-methyl-3,4-bis(5-methyl-1H-indol-3-yl)-2,5-dioxopyrrolodine (109 mg, 72.4%) as a mixture of two isomers (A:B=3:1) 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-69d2934b3a064763b70f06a008afec15
Source dataset
uspto-grants-2003_07
Patent number
US06589977B1

Reaction notes

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