Bicarbonate Ion → HCID 67003555, 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-(3-(4-methoxybenzyloxy)oxetan-3-yl)thiazole (Example 11G) (300 mg, 0.424 mmol) and 1-(2-(pyrrolidin-1-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Example 20A) (173 mg, 0.593 mmol) in N,N-dimethylformamide (3.97 mL) was added saturated aqueous bicarbonate solution (1.32 mL) followed by bis(triphenylphosphine)palladium dichloride (20.8 mg, 0.030 mmol). The mixture was heated to 70° C. for 4 hours, cooled to room temperature, and 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 residue was purified by flash chromatography on silica gel, eluting with a gradient of 0 to 10% methanol in dichloromethane, to afford the title compound. MS ESI(+) m/z 745.1 [M+H]+.

Provenance & Evidence