Methanol → (6-Methyl-1H-indazol-5-yl)methylamine

Participants

Reaction Steps

A solution of 6-methyl-1H-indazole-5-carbonitrile (preparation 32) (230 mg, 1.47 mmol) in THF (10 ml) under nitrogen was treated with a solution of lithium aluminium hydride (1N, 3.66 ml, 3.66 mmol) in THF at 0° C. The resultant mixture was stirred for 16 hr warming to room temperature, then treated with MeOH (12 ml), H2O (0.8 ml), NaOH (4N, 2 ml) and H2O (4 ml). The resultant precipitate was removed by filtration, washed with THF and purified by chromatography (SiO2, eluting with 90:10:1 CH2Cl2:MeOH:NH3) to give the desired product (71 mg, 30%). 1H NMR (CD3OD) δ 2.40 (s, 3H), 3.95 (s, 2H), 7.35 (s, 1H), 7.70 (s, 1H), 7.95 (s, 1H), LRMS m/z=162.0 (M+1)+.

Provenance & Evidence