Sodium Chloride → 3-Bromo-1-methyl-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione

HRID 1357094

Reaktionsgleichung

Reaktionsgleichung von HRID 1357094
[C:1](=O)([O-])[O-].[K+].[K+].CI.[Br:9][C:10]1[C:11]([N:13]([CH3:26])[C:14](=[O:25])[C:15]=1[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][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]([CH3:26])[C:14](=[O:25])[C:15]=1[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH3:1])[CH:17]=1)=[O:12]

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 97965023-bromo-4-(1H-indol-3-yl)-1-methyl-pyrrole-2,5-dione

Produkt 1

HCID 98184713-Bromo-1-methyl-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dioneAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Potassium carbonate (140 mg, 0.98 mmol) and methyl iodide (0.06 mL, 0.98 mmol) were added under ice cooling to 2-bromo-3-(1H-indol-3-yl)-N-methylmaleimide (100 mg, 0.33 mmol) synthesized according to a known method (Tetrahedron, Vol. 44, p. 2887, 1988) and dissolved in DMF (5 mL), and the whole was stirred for 2 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=1:1) to obtain 2-bromo-3-(1-methyl-1H-indol-3-yl)-N-methylmaleimide (99 mg, 95.1%) as red solids.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-e76ccb9cc94d4917a00169ccbccf2734
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06589977B1

Verknüpfte Notizen

Wird geladen…