Water → ethyl 1-(1,4-dioxepan-6-yl)-5-[4-(2-methoxy-3,5-dimethylpyridin-4-yl)-2-nitrophenyl]-1H-pyrazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

Water (0.2 mL), (2-methoxy-3,5-dimethylpyridin-4-yl)boronic acid (39.5 mg) obtained in Preparation Example 29, Pd(PPh3)4 (10.5 mg) and cesium carbonate (178 mg) were added to a solution of ethyl 5-(4-bromo-2-nitrophenyl)-1-(1,4-dioxepan-6-yl)-1H-pyrazole-4-carboxylate (80 mg) obtained in Preparation Example 9-(2) in 1,4-dioxane (1.3 mL), and the reaction mixture was stirred at 100° C. for 6.75 hours. (2-methoxy-3,5-dimethylpyridin-4-yl)boronic acid (15 mg) was added to the reaction mixture and the reaction mixture was stirred at 100° C. for 2.5 hours. After the reaction mixture was returned to mom temperature, ethyl acetate and water were added to the reaction mixture, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (silica gel, ethyl acetate/n-heptane, 20 to 33%) to give the title compound (64 mg).

Provenance & Evidence