Hydrochloric Acid → 1-{4-[1-(4-methoxyphenyl)-7-oxo-3-(trifluoromethyl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl]phenyl}cyclobutane carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Part C. The product from part B (1.20 g, 3.97 mmol) and 1-(4-methoxyphenyl)-3-(trifluoromethyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one (0.87 g, 2.8 mmol) were stirred in DMSO (3 mL) under N2. K2CO3 (1.16 g, mmol, 3.0 eq) was added followed by the addition of 1,10-phenanthroline (100 mg, 20 mol %) and CuI (106 mg, 20 mol %). The resulting mixture was stirred at 130° C. overnight. LC-MS showed completion of the reaction. EtOAc was added to the cooled solution. The solution was acidified with 1N HCl, and the organic layer was washed with H2O and and brine, dried over MgSO4, filtered, and concentrated to afford 1-{4-[1-(4-methoxyphenyl)-7-oxo-3-(trifluoromethyl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl]phenyl}cyclobutane carboxylic acid (1.34 g, yield 97%). LC/MS (ESI+) 486.6 (M+H)+, tR=2.81 min (10–90% CH3CN/H2O in a 4-min run).

Provenance & Evidence