Ngic-I → 12-(2-cyanoethyl)-6,7,12,13-tetrahydro-13-methyl-5-oxo-5H-indolo(2,3-a)pyrrolo(3,4-c)carbazole

HRID 2395707

Reaktionsgleichung

Reaktionsgleichung von HRID 2395707
[H-].[Na+].[C:3]([CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[NH:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[C:17]=3[C:16]3[C:27](=[O:30])[NH:28][CH2:29][C:15]=3[C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)#[N:4].[CH3:31]I>CN(C)C=O>[C:3]([CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[N:20]([CH3:31])[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[C:17]=3[C:16]3[C:27](=[O:30])[NH:28][CH2:29][C:15]=3[C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)#[N:4]

Komponenten

5

Edukt 3

HCID 3714Ngic-IHCID 6328Methyl iodideHCID 24758Sodium hydride

Produkt 1

HCID 350112-(2-cyanoethyl)-6,7,12,13-tetrahydro-13-methyl-5-oxo-5H-indolo(2,3-a)pyrrolo(3,4-c)carbazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

36 mg (1.2 mmole) sodium hydride (80% in mineral oil) are suspended under an atmosphere of nitrogen in 50 mL dry dimethylformamide and 365 mg (1 mmole) 12-(2-cyanoethyl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole added portionwise thereto at ambient temperature. After subsidence of the gas evolution, stirring is continued for 1 hour at 20° C. 0.08 mL (1.25 mmole) methyl iodide is then added thereto and stirring continued for 16 hours at ambient temperature. The solvent is distilled off in a vacuum and the residue is chromatographed on silica gel with toluene/ethanol (95:5 v/v). The fraction with an Rf of 0.3 in dichloromethane/methanol (95:5 v/v) is isolated and recrystallized from tetrahydrofuran. 12-(2-cyanoethyl)-6,7,12,13-tetrahydro-13-methyl-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole is obtained in the form of pale yellow crystals which decompose above 270° C.

Aufarbeitung

  1. customat ambient temperature
  2. stirringstirring
  3. waitcontinued for 16 hours at ambient temperature
  4. distillationThe solvent is distilled off in a vacuum
  5. customthe residue is chromatographed on silica gel with toluene/ethanol (95:5 v/v)
  6. customThe fraction with an Rf of 0.3 in dichloromethane/methanol (95:5 v/v) is isolated
  7. customrecrystallized from tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-0c2fb0beecac4bd7b384c974a08e8460
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05489608

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