tert-Butyl 7-nitro-1H-indazole-1-carboxylate → tert-Butyl 7-amino-1H-indazole-1-carboxylate

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A mixture of 7-Nitro-1-tert-butoxycarbonyl-indazole (1.000 g, 3.798 mmol), prepared as in Intermediate 25, and palladium on carbon (10 wt %, 0.10 g) in ethyl acetate (25 mL) at ambient temperature is stirred under atmospheric hydrogen overnight. The mixture is filtered through celite and concentrated in vacuo to an oil which solidified under high vacuum to provide the title compound as a purple solid (0.860 g, 3.686 mmol). 1H NMR (300 MHz, d6-DMSO) δ=1.59 (b, 9H); 6.13 (b, 2H); 6.76 (d, J=7.6 Hz, 1H); 6.97 (d, J=7.6 Hz, 1H); 7.04-7.07 (m, 1H); 8.24 (s, 1H). TLC: Rf =0.47 (25:75 ethyl acetate: n-hexane).

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