HCID 67002664, compound → HCID 67003885, compound

Participants

Reaction Steps

A solution of 1-(5-(5-fluoro-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol (150 mg, 0.263 mmol), 5-(5-(tributylstannyl)thiazol-2-yl)-4-oxa-1-azabicyclo[3.2.1]octane (192 mg, 0.395 mmol), and bis(triphenylphosphine)palladium dichloride (0.013 g, 0.025 mmol) in N,N-dimethylformamide (1.8 mL) was heated to 70° C. for 2 hours. The reaction was quenched by the addition of an aqueous potassium fluoride solution (1.0 g in 2.5 mL water) and ethyl acetate (5 mL). The mixture was stirred vigorously overnight and was then filtered through diatomaceous earth, eluting with ethyl acetate. The layers were separated, and the organic layer was washed with aqueous saturated sodium bicarbonate and water. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used without further purification. MS ESI(+) m/z 638.2 [M+H]+.

Provenance & Evidence