Bromoacetic Acid → [1-(4-Methoxy-phenyl)-7-oxo-3-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-acetic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

Part A: 1-(4-Methoxy-phenyl)-3-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one (2.0 g, 6.43 mmol) was stirred in dry DMF (8 mL) at 0° C. NaH (60%, 0.35 g, 8.75 mmol, 1.4 eq) was added. Bromoacetic acid and t-butyl ester (1.0 mL, 6.77 mmol, 1.1 eq) were added dropwise. The mixture was stirred at 0° C. for 2 h and at rt overnight. The reaction was quenched with H2O, extracted with EtOAc, washed with brine, concentrated, and purified by silica gel chromatography (1:1 EtOAc:hexanes) to give pure [1-(4-methoxy-phenyl)-7-oxo-3-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-acetic acid tert-butyl ester (2.73 g, yield: 99%).

Provenance & Evidence