Potassium Phosphate, Tribasic → tert-butyl 4-(3-(2-(2,4-difluorophenoxy)-5-nitrophenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl)-5,6-dihydropyridine-1 (2H)-carboxylate

Participants

Reaction Steps

A mixture of Example 182B (238 mg, 0.485 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (150 mg, 0.485 mmol), phenylallylchloro[1,3-bis(diisopropylphenyl)-2-imidazol-2-ylidene]palladium(II) (31.4 mg, 0.048 mmol) and potassium phosphate (309 mg, 1.454 mmol) in 9 mL tetrahydrofuran and 3 mL water was heated at 60° C. for 3 hours. Water was added, extracted with ethyl acetate (3×), washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel with a gradient of 0-50% ethyl acetate in heptanes to give the title compound (212 mg, 0.358 mmol, 73.8% yield) as a yellow solid.

Provenance & Evidence