1-benzyl-3,4-bis(1H-indol-3-yl)pyrrole-2,5-dione → HCID 10550007, compound

HRID 1357109Notes

Reaction equation

HRID 1357109 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[C:11]([N:13]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:14](=[O:25])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:12])=[CH:2]1>CN(C=O)C.[C].[Pd]>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH:15]([C:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)[C:14](=[O:25])[N:13]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:11]2=[O:12])=[CH:2]1

Participants

4

Reactant 1

HCID 113620681-benzyl-3,4-bis(1H-indol-3-yl)pyrrole-2,5-dione

Product 1

HCID 10550007HCID 10550007, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,3-bis(1H-indol-3-yl)-N-benzylmaleimide (35 mg, 0.084 mmol) in DMF (1 mL) was added a small amount of 10% palladium-carbon, and the whole was stirred at room temperature for 6 hours 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(1H-indol-3-yl)-1-benzyl-2,5-dioxopyrrolidine (32.1 mg, 91.3%) 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-66243a354b8c4b35bb3af58e238d4fff
Source dataset
uspto-grants-2003_07
Patent number
US06589977B1

Reaction notes

Loading…