Bicarbonate Ion → HCID 86659279, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred ambient solution of 1-(5-(5-chloro-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol (Example 8A) (2.85 g, 4.86 mmol) and 4-formylphenylboronic acid (1.094 g, 7.30 mmol) in N,N-dimethylformamide (36.5 ml) was added saturated aqueous bicarbonate solution (12.16 ml) followed by bis(triphenylphosphine)palladium dichloride (0.239 g, 0.341 mmol). The mixture was heated to 70° C. for 2 hours, cooled to room temperature, and 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 70% ethyl acetate in hexane, to afford the title compound. MS ESI(+) m/z 564.5 [M+H]+.

Provenance & Evidence