Ammonium Chloride → 3-cyclopropyl-1-((1-isopropyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine

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To a mixture of 3-cyclopropyl-1-((1-isopropyl-1H-pyrazol-3-yl)methyl)-4-nitro-1H-indazole (1.08 g, 3.32 mmol), ammonium chloride (88.8 mg, 1.66 mmol) in 4:1 EtOH/water (15 mL) was added iron powder (1.85 g, 33.2 mmol) and the mixture was heated at reflux for 3 hours. The solvent was removed under reduced pressure and the residue was mixed with in EtOAc/water and filtered through GF/F paper. The organic phase was separated and concentrated under reduced pressure to provide 3-cyclopropyl-1-((1-isopropyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine (0.815 g, 83% yield) as a yellow solid.

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