HCID 67256279, compound → HCID 67257668, compound

Participants

Reaction Steps

Tert-butyl (1-(4-(5-nitro-6-oxo-3-phenyl-1,6-dihydropyridin-2-yl)phenyl)cyclobutyl)carbamate (10.95 g, 23.77 mmol) was dissolved in acetic acid (250 mL) at room temperature. Zinc powder (10 g, 153 mmol) was added at 30° C. and the resulting suspension was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure and the obtained residue was partitioned between water (250 mL) and ethyl acetate (250 mL). The aqueous phase was extracted with fresh ethyl acetate (3×200 mL) and the combined organic layers were washed with water (200 mL), brine (200 mL), dried on anhydrous Na2SO4, filtered and concentrated to dryness under reduced pressure. The obtained crude was purified by Biotage silica gel chromatography (gradient 0% to 3% methanol in dichloromethane) to give the title compound (4.3 g, 43%). It was used for the next step without further purification. LCMS (Method A) RT 5.96 min, M+1=432.

Provenance & Evidence