Sodium Carbonate → tert-butyl 1-(4-(8-(1-isobutyl-1H-pyrazol-4-yl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate (0.050 g, 0.1 mmol), sodium carbonate (0.032 g, 0.3 mmol) and 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.025 g, 0.100 mmol) were dissolved in dioxane (5 mL) and water (1 mL). The reaction mixture was degassed, PdCl2(dppf)-CH2Cl2 adduct (0.012 g, 0.0150 mmol) added and heated at 80° C. After 16 hours, the reaction mixture was filtered through Celite®, washed with ethyl acetate, evaporated and purified by column chromatography using 0-40% ethyl acetate in hexane to give the title compound (40 mg, 68%). LC-MS (Method I): RT=8.27 min, [M+H]+=591.

Provenance & Evidence