Lithium Hydroxide → 7-methoxy-1H-indazole-5-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 7-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxylate (980 mg, 4.45 mmol) in THF (10 mL), water (10 mL) and LiOH (560 mg, 13.4 mmol) was heated at 40° C. for 3 hours and then stirred at room temperature overnight. The reaction was not complete so the mixture was heated to 45° C. and heated overnight. The mixture was then concentrated to dryness, acidified to pH 6 with conc. HCl and partitioned between EtOAc and water. The resultant solids were collected by vacuum filtration, rinsed with EtOAc and dried under high vacuum to afford a white solid. The organic layer was washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to provide an off-white solid. Both batches of white solid were combined to afford the title compound (642 mg, 75%).

Provenance & Evidence