Hydrochloric Acid → HCID 70816631, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-(5-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonitrile (3.09 g, 10.27 mmol, 1.0 eq) in THF (40 mL) was added BH3-DMS (2.30 g, 30.81 mmol, 3.0 eq) at 0° C. and heated to reflux for 1 h. The reaction mixture was cooled to 0° C. and quenched with 1N HCl and basified with 1N solution of NaOH to a pH of ˜10 and the mixture extracted with ethyl acetate (100 mL×2), dried (Na2SO4), the solvent evaporated to get a pale yellow oil. The oil was treated with ether and HCl to get (1-(5-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (1.3 g, 20% yield over 3 steps) as white solid (TLC system: CHCl3/MeOH (9:1), Rf 0.5).

Provenance & Evidence