Sodium Chloride → 2-bromo-3-(1,5-dimethyl-1H-indol-3-yl)-N-methylmaleimide

HRID 1357103

Reaction equation

HRID 1357103 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[Br:9][C:10]1[C:11]([N:13]([CH3:27])[C:14](=[O:26])[C:15]=1[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH3:25])[CH:23]=2)[NH:18][CH:17]=1)=[O:12].[Cl-].[Na+]>CN(C=O)C>[Br:9][C:10]1[C:11]([N:13]([CH3:27])[C:14](=[O:26])[C:15]=1[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH3:25])[CH:23]=2)[N:18]([CH3:1])[CH:17]=1)=[O:12]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 98835102-bromo-3-(5-methyl-1H-indol-3-yl)-N-methylmaleimide

Product 1

HCID 185054442-bromo-3-(1,5-dimethyl-1H-indol-3-yl)-N-methylmaleimideYield 96.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (130 mg, 0.94 mmol) and methyl iodide (0.06 mL, 0.94 mmol) were added under ice cooling to 2-bromo-3-(5-methyl-1H-indol-3-yl)-N-methylmaleimide (100 mg, 0.31 mmol) dissolved in DMF (5 mL), and the whole was stirred for 1.5 hours. The reaction mixture was warmed to room temperature, added with saturated aqueous sodium chloride solution, and extracted with ethyl acetate. The extract was dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by column chromatography over silica gel (ethyl acetate:n-hexane=1:2) to obtain 2-bromo-3-(1,5-dimethyl-1H-indol-3-yl)-N-methylmaleimide (100 mg, 95.8%) as red solids.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography over silica gel (ethyl acetate:n-hexane=1:2)

Sources & evidence

ORD record
ord-ebb5ce321cad43c6a914920f2a4565a8
Source dataset
uspto-grants-2003_07
Patent number
US06589977B1

Linked notes

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