Formic Acid → HCID 90077264, compound

Participants

Reaction Steps

6-chloro-2-(((4aR,7R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)oxy)-1-((2-(trimethylsilyl)ethoxy)methyl)-5-(4-((trimethylsilyl)ethynyl)phenyl)-1H-imidazo[4,5-b]pyridine (220 mg, 0.319 mmol) was dissolved in formic Acid (4.5 ml, 117 mmol) and sat. potassium hydrogen sulfate (0.5 ml, 0.319 mmol). The mixture was stirred at rt for 1 h, and then diluted with EtOAc. Then 3 M NaOH was added until a pH of pH 14 was reached. The mixture was stirred for 15 minutes at rt and then the layers were separated. The aqueous phase was extracted with EtOAc (×2). The combined organic extracts were washed with brine and dried over Na2SO4, filtered and concentrated. The resulting crude product was purified by column chromatography on Biotage™ 25 g column by eluting with 50% EtOAc in DCM to yield the title compound. LC-MS: m/e=400.32 (M+H)+ (Rt 1.71/4 min).

Provenance & Evidence