tert-Butyl 5-Nitro-1H-indazole-1-carboxylate → 1,1-Dimethylethyl 5-amino-1H-indazole-1-carboxylate

Participants

Reaction Steps

In a Paar flask charged with palladium (10 wt % on carbon, 0.44 g) was added ethyl acetate (30 mL) and 5-nitro-indazole-1-carboxylic acid t-butyl ester (1.61 g, 6.2 mmol). The reaction mixture was hydrogenated at 50 psi for 30 minutes with vigorous shaking. The reaction mixture was filtered through a plug of celite. The plug was washed with 20 mL of methanol and the combined filtrates were concentrated in vacuo to give a white solid (1.4 g, 100%). 1H NMR (300 MHz, CDCl3), δ: 7.99 (s, 1H), 7.97 (d, J=10, 1H), 6.94 (dd, J=10, J′=2, 1H), 6.92 (d, J=2, 1H), 1.71 (s, 9H).

Provenance & Evidence