Sodium Hydroxide → 4-(2-Fluoro-4-iodophenylamino)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-(2-fluoro-4-iodophenylamino)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (380 mg, 0.71 mmol) in IMS (10 mL) was added aqueous sodium hydroxide solution (1.78 mL, 1M, 1.78 mmol). The reaction mixture was heated at 65° C. for 2 hours, during which time all solids dissolved. Volatile solvents were removed in vacuo and the resultant solution was acidified to pH ˜3 by careful addition of aqueous hydrochloric acid (1M) causing a precipitate to form. The precipitate was collected by filtration and dried under vacuum at 45° C. to yield the title compound as a brown solid (360 mg, 100%). LCMS (Method B): RT=3.84 min, [M+H]+=519.

Provenance & Evidence