tert-Butyl 3-amino-5-nitro-1H-indazole-1-carboxylate → tert-butyl 3,5-diamino-1H-indazole-1-carboxylate

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Reaction Steps

3-Amino-5-nitroindazole-1-carboxylic acid tert-butyl ester (3 g, 10.8 mmol) was dissolved in MeOH (50 mL) and the solution degassed (3× alternating vacuum/nitrogen purges). Palladium on charcoal 10% w/w (300 mg) was added and the nitrogen atmosphere replace by hydrogen. After 3 hours, the mixture was filtered through a pad of Celite® and the filtrate concentrated to afford the title compound as a highly viscous oil (2.17 g, 81%). 1H NMR (400 MHz, DMSO)1.55 (9H, s), 5.07 (2H, brs), 6.04 (2H, brs), 6.79–6.82 (2H, m), 7.62 (1H, brs). MS (ES+) m/e=249.

Provenance & Evidence