(Diethylamino)sulfur trifluoride → HCID 67003540, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (0° C.) solution of 1-(5-(5-chloro-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol (Example 8A) (330 mg, 0.563 mmol) in dichloromethane (6 mL) and dioxane (6 mL) was added diethylaminosulfur trifluoride (0.149 mL, 1.127 mmol) in a single portion via syringe. The reaction was stirred at 0° C. for 2 hours and was then quenched by the addition of saturated sodium bicarbonate solution and ethyl acetate. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×). The combined organics were dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of hexane to 25% ethyl acetate in hexane, to give the title compound. 1H NMR (300 MHz, DMSO-d6) 8.51 (s, 1H), 8.24 (d, J=2.8 Hz, 1H), 7.97 (d, J=8.4 Hz, 2H), 7.47 (d, J=8.0 Hz, 2H), 7.24 (s, 1H), 2.80-2.63 (m, 4H), 2.37 (s, 3H), 2.09-1.96 (m, 1H), 1.94-1.85 (m, 1H).

Provenance & Evidence