Bicarbonate Ion → HCID 67003666, 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-fluorocyclobutyl)thiazole (Example 114A) (60 mg, 0.102 mmol) and 4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethyl)morpholine (37.6 mg, 0.122 mmol) in N,N-dimethylformamide (0.765 mL) was added saturated aqueous bicarbonate solution (0.765 mL) followed by bis(triphenylphosphine)palladium dichloride (5.01 mg, 7.14 μmol). 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. MS ESI(+) m/z 641.2 [M+H]+.

Provenance & Evidence