Bisindolylmaleimide V → HCID 496503, compound

HRID 1357091Notes

Reaction equation

HRID 1357091 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]([CH3:26])[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]([CH3:26])[C:11]2=[O:12])=[CH:2]1

Participants

4

Reactant 1

HCID 2400Bisindolylmaleimide V

Product 1

HCID 496503HCID 496503, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,3-bis(1H-indol-3-yl)-N-methylmaleimide (14 mg, 0.04 mmol) synthesized according to a known method (Tetrahedron, Vol. 44, p. 2887, 1988) in DMF (1 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(1H-indol-3-yl)-1-methy-2,5-dioxopyrrolidine (12.9 mg, 91.7%) as a mixture of two isomers (A:B=2.7:1.0) 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-31d1774ff88d48b8b3f8d5fb9b3d6036
Source dataset
uspto-grants-2003_07
Patent number
US06589977B1

Reaction notes

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