Dimethylformamide → N-methyl-7-azaindole

HRID 226034

Reaktionsgleichung

Reaktionsgleichung von HRID 226034
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[CH3:10]N(C=O)C.[H-].[Na+].CI>CCOC(C)=O>[CH3:10][N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 24758Sodium hydride

Produkt 1

HCID 583068N-methyl-7-azaindoleAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1H-pyrrolo[2,3-b]pyridine (1.00 g, 8.46 mmol) and DMF (10 mL) is added 60% NaH (0.41 g, 10.16 mmol). After 30 min, MeI (0.63 mL, 10.16 mmol) is added and the solution stirred for 1 h. The solution is diluted with EtOAc (60 mL), washed with water (2×50 mL), brine (50 mL), dried aver MgSO4, filtered and concentrated to furnish the title compound (1.10 g, 0.83 mmol, 99%). 1H NMR (CDCl3), δ 3.90 (s, 3H), 6.45 (d, J=3.5 Hz, 1H), 7.05 (dd, J=8.1, 4.6 Hz, 1H), 7.17 (d, J=3.5 Hz, 1H), 7.90 (d, J=7.7, 1.8 Hz, 1H), 8.40 (dd, J=4.8, 1.3 Hz, 1H). LC/MS (m/z): calcd. for C8H8N2 (M+H)+: 133.2. found.

Aufarbeitung

  1. washwashed with water (2×50 mL), brine (50 mL)
  2. dry with materialdried aver MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b7bcef21d1514874b508c03b6185e987
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557103B2

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