Water → 6-bromo-2-(2-fluorobenzyl)-2H-indazol-3-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-2-fluorobenzonitrile (3.19 g, 15.64 mmol) and diisopropylamine (13.16 mL, 93.86 mmol) in n-butanol (70 mL) was added (2-fluorobenzyl)hydrazine dihydrochloride (10 g, 46.93 mmol) and the very thick slurry was heated to 125° C. (the mixture became a cloudy solution at 90° C.) for 18 h. The reaction mixture was poured into water and ethyl acetate. The organic layer was isolated and washed with brine, dried over Na2SO4 and concentrated. The resulting light brown solid was taken up in DCM (60 mL) and the suspension stirred for 15 min and filtered. The filter cake was washed with very little DCM and hexanes and dried on a high vacuum pump to give the product as a light brown solid (1.55 g, 31%). LC-MS [M+H]+=320.3, 322.3, RT=2.33 min.

Provenance & Evidence