Lithium Hydroxide → (R)-5-(2-(3-carboxy-5-fluorophenyl)-4,4-difluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of (R)-ethyl 5-(2-(3-cyano-5-fluorophenyl)-4,4-difluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylate (X-8) (90 mg, 0.22 mmol) in THF:MeOH:H2O 3:2:1 (2.5 mL) was added LiOH (46 mg, 1.1 mmol) and stirred at 50° C. for 12 hours. The reaction was subsequently neutralized and concentrated to dryness. The crude product was purified by column chromatography on silica gel with DCM/MeOH gradient as eluant to yield (R)-5-(2-(3-carboxy-5-fluorophenyl)-4,4-difluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylic acid (I-52), which was immediately used in the next reaction. MS m/z 406.1 (M+1)+.

Provenance & Evidence