Iodine → HCID 67003444, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (−78° C.) solution of 5-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-(1-(methoxymethoxy)cyclobutyl)thiazole (Example 1E) (5.0 g, 9.92 mmol) in tetrahydrofuran (50 mL) was added a solution of lithium diisopropylamide (13.9 mmol) in tetrahydrofuran (15 mL). The reaction was stirred at −78° C. for 1 hour, and a solution of iodine (3.52 g, 13.89 mmol) in tetrahydrofuran (10 mL) was added. The cold bath was removed, and, after 15 minutes, the reaction was quenched by the addition of saturated aqueous sodium thiosulfate 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 0 to 30% ethyl acetate in hexane, to give the title compound. MS ESI(+) m/z 586 [M+H]+;

Provenance & Evidence