Water → HCID 59355376, compound

Participants

Reaction Steps

3-Amino-2-bromo-6-chloroisonicotinic acid methyl ester (500 mg), potassium carbonate (829 mg), tetrakis(triphenyl phosphine)palladium(0) and trimethylboroxine (276 mg) were suspended in dioxane (15 mL). Water (1.5 mL) was added and the mixture was degassed using subsequent evaporation and flushing with nitrogen (5×). The reaction mixture was stirred under reflux for 7 hours. After cooling to room temperature, the mixture was quenched with water and extracted 2× with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica 60, hexane/ethyl acetate=3:1, Rf=0.25) to afford 100 mg of the title compound of the formula

Provenance & Evidence