Ammonium Chloride → 3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazole-4-amine

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To a suspension of 3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole (22.01 g, 71.38 mmol) in EtOH/H2O (200 mL/50 mL) was added iron powder (79.73 g, 1428 mmol) and NH4Cl (3.818 g, 71.38 mmol). The reaction mixture was heated to reflux for three hours, cooled to 60° C. and filtered through a pad of Celite. The pad of Celite was washed with 20:1 EtOH/Et3N (800 mL) and 1:1 MeOH/DCM (600 mL). The combined filtrate was concentrated under reduced pressure. The residue was dissolved in EtOAc (800 mL), washed with saturated NaHCO3 aqueous solution, dried (Na2SO4) and concentrated under reduced pressure to give the product (16.87 g).

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