Formic Acid → (2R,3 S,5R)-5-((5-(4-bromophenyl)-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl)oxy)-2-(hydroxymethyl)-tetrahydro-2H-pyran-3-ol

Participants

Reaction Conditions

Reaction Steps

5-(4-bromophenyl)-6-chloro-2-(((4aR,7R,8aS)-2-phenylhexahydropyrano-[3,2-d][1,3]dioxin-7-yl)oxy)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridine (1.5 g, 2.229 mmol) was dissolved in formic acid (30 ml, 782 mmol) and aqueous saturated KHSO4 (2 mL). The reaction was heated to 50° C. overnight, then diluted with EtOAc, followed by the addition of 3M NaOH until a pH of ˜13 was reached. After stirring 10 min at rt, saturated NH4Cl was added until a pH of ˜7 was reached. The aqueous phase was separated, and extracted with EtOAc (×2). The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The resulting residue was purified by column chromatography on a Biotage™ 50 g column by eluting with 1% to 12% MeOH in CHCl3. LC-MS: calculated for C18H17BrClN3O4 453.01 observed m/e: 453.94 (M+H)+ (Rt 1.13/2 min).

Provenance & Evidence