Methanol → HCID 18505443, compound

HRID 1357093Notes

Reaction equation

HRID 1357093 reaction equation
[CH3:1][N:2]([CH3:32])[CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[C:16]([N:18]([CH3:31])C(=O)[C:20]=2C2C3C(=CC=CC=3)NC=2)=[O:17])=[CH:7]1.[CH3:33][OH:34]>[C].[Pd]>[CH3:32][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2([C:8]3[C:9]4[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=4)[NH:6][CH:7]=3)[CH2:20][C:33](=[O:34])[N:18]([CH3:31])[C:16]2=[O:17])=[CH:7]1

Participants

4

Reactant 2

HCID 887MethanolHCID 18505441HCID 18505441, compound

Product 1

HCID 18505443HCID 18505443, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

To a solution of 2-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-N-methylmaleimide (60 mg, 0.14 mmol) in MeOH (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 (dichloromethan:methanol=8:1) to obtain 3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-1-methyl-2,5-dioxopyrrolidine (49 mg, 81.5%) 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 (dichloromethan:methanol=8:1)

Sources & evidence

ORD record
ord-f84fe43c53f54aeba8b7455c3b506206
Source dataset
uspto-grants-2003_07
Patent number
US06589977B1

Reaction notes

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