Methyl iodide → N-methyl-7-azaindole

HRID 53165

Reaktionsgleichung

Reaktionsgleichung von HRID 53165
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[H-].[Na+].I[CH3:13]>CN(C)C=O>[CH3:13][N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 24758Sodium hydride

Produkt 1

HCID 583068N-methyl-7-azaindoleAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Pyrrolo[2,3-b]pyridine (2.00 g, 16.93 mmol) is dissolved in dimethylformamide (15.0 ml) under an argon atmosphere. Sodium hydride (60% in oil) (0.96 g, 40.0 mmol, 1.5 equiv.) is added at 0° C. over a period of 30 minutes. After 30 minutes' stirring at 0° C., iodomethane (1.49 ml, 24.02 mmol, 1.5 equiv.) is added dropwise. After returning to room temperature, the reaction mixture is stirred for 1 hour. The dimethylformamide is evaporated off under reduced pressure, and the product is taken up in water and extracted with dichloromethane. Purification on a silica column (petroleum ether/ethyl acetate 7/3) allows isolation of the title compound in the form of an oil in a yield of 99%. ##STR31##

Aufarbeitung

  1. customAfter returning to room temperature
  2. stirringthe reaction mixture is stirred for 1 hour
  3. customThe dimethylformamide is evaporated off under reduced pressure
  4. extractionextracted with dichloromethane
  5. customPurification on a silica column (petroleum ether/ethyl acetate 7/3)

Quellen und Nachweise

ORD-Eintrag
ord-f98ed61670bb41d79b57c957601641d5
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618819

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