1-({5-Chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-4-nitro-1H-pyrazole → 1-({5-Chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-4-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-({5-chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-4-nitro-1H-pyrazole (for a preparation see intermediate 8; 476 mg, 1.39 mmol) in ethanol (15 ml) was added stannous chloride (hydrated) (1.59 g, 7.03 mmol) and the reaction stirred at 85° C. overnight, under nitrogen. The reaction mixture was applied to a 20 g SCX-2 cartridge (pre-washed with MeOH) and the cartridge washed with methanol (6 column volumes). The product was eluted with 10% NH3 (aqueous) in MeOH (4 column volumes). The combined basic fractions were concentrated in vacuo. The residue was loaded in dichloromethane and purified on silica (50 g) using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound (191 mg) as a red gum; LCMS (System 1): MH+=314, tRET=2.69 min.

Provenance & Evidence