Ammonium Chloride → 1-(4-amino-phenyl)-3-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-yl]-urea

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A mixture of 1-(4-nitro-phenyl)-3-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-yl]-urea (3.1 g, 7.8 mmol), iron powder (3.5 g, 63 mmol), and ammonium chloride (0.21 g, 3.9 mmol) in a 4:1 ethanol/H2O solution (50 mL) was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was taken up and stirred in triethylamine/ethyl acetate (1/4, 30 mL) for 15 minutes followed by filteration through a plug of silica gel which was rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated under reduced pressure to provide the title compound (2.6 g, 92%). 1H NMR (300 MHz, DMSO-d6) ppm 1.89 (m, 4H), 3.06 (m, 4H), 3.64(m, 2H), 4.75 (d, J=6.44, 2H), 6.52 (m, 2H), 7.09 (m, 2H), 7.39 (m, 1H), 7.66 (m, 1H), 7.92 (m, 1H), 8.06 (s, 1H), 8.31 (m, 1H), 8.70 (s, 1H); MS (DCI/NH3) m/z 365 [M+H]+.

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