Hydrochloric Acid → N-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}benzene-1,2-diamine

Participants

Reaction Steps

To a solution of 100 mg (0.23 mmol) of (2-nitrophenyl)-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}amine in 10 mL of methanol was added 304 mg (4.65 mmol) of zinc powder followed by the addition of 4.65 mL (4.65 mmol) of 1 N aqueous HCl. After 1 hour, the mixture was made basic with saturated aqueous sodium bicarbonate and extracted with three 15 mL portions of ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by prep-TLC using 10-20% EtOAc/hexanes to provide 10 mg (14%) of the title compound as a white solid. MS m/z 401 (MH+).

Provenance & Evidence