HCID 9885647, compound → HCID 18505449, compound

HRID 1357097Notes

Reaction equation

HRID 1357097 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12]([N:14]([CH3:28])[C:15](=[O:27])[C:16]=2[C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH3:26])[CH:18]=2)=[O:13])=[CH:3]1>CN(C=O)C.[C].[Pd]>[CH3:28][N:14]1[C:15](=[O:27])[CH:16]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH3:26])[CH:18]=2)[CH:11]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)[C:12]1=[O:13]

Participants

4

Reactant 1

HCID 9885647HCID 9885647, compound

Product 1

HCID 18505449HCID 18505449, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,3-bis(1-methyl-1H-indol-3-yl)-N-methylmaleimide (50 mg, 0.14 mmol) 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 1-methyl-3,4-bis(1-methyl-1H-indol-3-yl)-2,5-dioxopyrrolidine (28 mg, 55.7%) as pale red solids. 1H-NMR(CDCl3): δ 3.28(s, 3H), 3.44(s, 6H), 4.81(s, 2H), 6.63(s, 2H), 6.85-7.00(m, 2H), 7.04-7.11(m, 4H), 7.22-7.26(m, 2H).

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-0ab3427862c54a129ac72ca3a521591b
Source dataset
uspto-grants-2003_07
Patent number
US06589977B1

Reaction notes

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