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

HRID 1357103

Reaktionsgleichung

Reaktionsgleichung von HRID 1357103
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 185054442-bromo-3-(1,5-dimethyl-1H-indol-3-yl)-N-methylmaleimideAusbeute 96,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-ebb5ce321cad43c6a914920f2a4565a8
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06589977B1

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