HCID 67088872, compound → HCID 178508018, compound

Participants

Reaction Steps

SnCl2 dihydrate (0.243 g, 1.28 mmol) was added to a suspension of 5-nitro-N-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridin-3-amine (0.099 g, 0.257 mmol) in ethyl acetate (25 mL), and the reaction mixture was heated to reflux overnight. The reaction mixture was cooled to room temperature and quenched with saturated aqueous NaHCO3 (25 mL). The resulting suspension was filtered through a pad of celite, and the filter cake was washed with ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (1:1), hexanes/ethyl acetate (1:2) to give N3-phenyl-1H-pyrazolo[3,4-b]pyridine-3,5-diamine (0.012 g, 21% over 3 steps) as solids.

Provenance & Evidence