Tetrahydrofuran → HCID 86659280, compound

Participants

Reaction Steps

To an ambient solution of 3-(4-(5-chloro-4-(2-(1-(methoxymethoxy)cyclobutyl)thiazol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-pyrazol-1-yl)propane-1,2-diol (Example 14B) (1.28 g, 1.987 mmol) in a solvent mixture of tetrahydrofuran (14.90 mL) and water (4.97 mL) was added solid sodium periodate (0.638 g, 2.98 mmol) in a single portion. The reaction was stirred at room temperature for 1 hour 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 once with 10% aqueous sodium thiosulfate solution (10 mL), dried with anhydrous sodium sulfate, filtered and concentrated to give the title compound, which was used in the next step without further purification. MS ESI(−) m/z 610.2 [M−H]−.

Provenance & Evidence