Water → HCID 66680081, compound

Participants

Reaction Steps

0.67 g (5.4 mmol) of 4-pyridine boronic acid, 1.0 g (2.7 mmol) of methyl 2-{[(3-bromophenyl)carbonyl]amino}-5-chlorobenzoate, 313 mg (0.27 mmol) of tetrakis(triphenylphosphine)palladium(0), and 0.58 g (5.4 mmol) of sodium carbonate were heated under reflux in a mixed solvent of 4 mL of water, 23 mL of toluene, and 6.7 mL of methanol for 7.5 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure. Ethyl acetate was added, and solids were collected by filtration. Subsequently, the organic layer was washed with saturated saline and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography, thereby giving 320 mg of methyl 5-chloro-2-({[3-(pyridin-4-yl)phenyl]carbonyl}amino)benzoate (yield: 32%).

Provenance & Evidence