Ammonium Chloride → 1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-amine

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-4-nitro-1H-indazole (1.51 g, 4.87 mmol) in EtOH/H2O (40 mL/10 mL) was added iron (5.43 g, 97.3 mmol) and ammonium chloride (0.260 g, 4.87 mmol). The reaction mixture was heated to reflux for three hours, then cooled to 60° C. and filtered through a pad of Celite®. The filter cake was washed with EtOH/Et3N (20:1, 200 mL) and MeOH/DCM (1:1, 100 mL). The filtrate was concentrated, and the residue was dissolved in EtOAc (200 mL). The ethyl acetate was washed with NaHCO3, dried (Na2SO4), filtered and concentrated to give the desired product (57%).

Provenance & Evidence