Bicarbonate Ion → HCID 67003839, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred ambient solution of 5-(5-chloro-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-(1-(methoxymethoxy)cyclobutyl)thiazole (Example 1F) (200 mg, 0.318 mmol) and 4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethyl)morpholine (127 mg, 0.413 mmol) in N,N-dimethylformamide (0.79 mL) was added saturated aqueous bicarbonate solution (0.79 mL) followed by bis(triphenylphosphine)palladium dichloride (15.60 mg, 0.022 mmol). The mixture was heated to 70° C. for 4 hours and was then quenched by the addition of water and ethyl acetate. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate. The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel, eluting with a gradient of 20% ethyl acetate in hexane to 100% ethyl acetate with 3% methanol, to afford the title compound. MS ESI(+) m/z 683.52 [M+H]+.

Provenance & Evidence