Acetone → HCID 67003853, compound

Participants

Reaction Steps

To an ambient solution of 5-(2-(1-allyl-1H-pyrazol-4-yl)-5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-(1-(methoxymethoxy)cyclobutyl)thiazole (Example 14A) (1.5 g, 2.458 mmol) in a solvent mixture of acetone (6.15 mL) and water (2.05 mL) was added potassium osmate (VI) dihydrate (9.06 mg, 0.025 mmol) followed by N-methylmorpholine-N-oxide (0.288 g, 2.458 mmol). The reaction was stirred overnight and was then quenched by the addition of 10% aqueous sodium thiosulfate solution (10 mL) and ethyl acetate (15 mL). The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×15 mL). The combined organics were washed with 10% aqueous sodium thiosulfate solution (10 mL), dried with anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 0 to 10% methanol in dichloromethane, to give the title compound. MS ESI(+) m/z 642.2 [M+H]+.

Provenance & Evidence