Dimethylformamide → N-methyl-7-azaindole

Participants

Reaction Steps

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.

Provenance & Evidence