Ammonium Chloride → 1-(3-(trifluoromethyl)benzyl)-1H-indazol-4-amine

Participants

Reaction Steps

To a round bottom flask was added 3-iodo-4-nitro-1-(3-(trifluoromethyl)benzyl)-1H-indazole (0.540 g, 1.21 mmol) and MeOH (12 mL). Zinc dust (0.395 g, 6.04 mmol) was added followed by saturated aqueous NH4Cl (12 mL). The mixture was stirred vigorously at ambient temperature for 2 hours. The reaction mixture was filtered and the solids were washed with EtOAc (30 mL). Saturated aqueous NH4OAc (25 mL) was added to the filtrate and the mixture was concentrated to remove organic solvents. The aqueous phase was then extracted with EtOAc (3×20 mL). The combined organic extracts were washed with a saturated aqueous NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated. The crude residue was purified by 1 mm preparative TLC using 5% MeOH/CH2Cl2 to afford 0.120 g (34%) of the product as a dark yellow/orange oil.

Provenance & Evidence