1H-Indazole-3-carboxylic acid, 1-methyl- → 1-(1-Methyl-1H-indazol-3-yl)ethan-1-one

Participants

Reaction Steps

Methyl lithium (1.58M solution in ether; 13.8 ml) was added dripwise to a stirred, cold (-60°) solution of 1-methyl-1H-indazole-3-carboxylic acid (1.77 g) in dry THF (60 ml) under nitrogen and stirring was continued while warming to 0° over 2 h. The reaction mixture was quenched with saturated ammonium chloride solution (50 ml), and the layers were separated. The aqueous layer was further extracted with dichloromethane (2×50 ml ) and the combined organic layers were washed with brine (2×50 ml ), dried and evaporated in vacuo. The residual solid (1.8 g) was purified by FCC eluting with System B (1:4) to give the title compound (1.3 g, m.p. 86°-88°.

Provenance & Evidence