Cesium carbonate → HCID 67343884, compound

Participants

Reaction Conditions

Reaction Steps

0.10 g of 2,6-difluorophenylboronic acid, 0.52 g of cesium carbonate, 2.4 mg of palladium acetate and 2.2 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl were added to 2.5 mL of toluene solution containing 0.20 g of tert-butyl 2-(benzamido)-4-bromobenzoate at room temperature sequentially, and stirred under nitrogen atmosphere at 80° C. for 1 hour and 10 minutes and then heated to reflux for 1 hour. After the reaction mixture was cooled to room temperature, 2.4 mg of palladium acetate and 2.2 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl were added and the resulting mixture was heated to reflux under nitrogen atmosphere for 1 hour. After the reaction mixture was cooled to room temperature, 2.4 mg of palladium acetate and 2.2 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl were added and the resulting mixture was heated to reflux under nitrogen atmosphere for 1 hour. After the reaction mixture was cooled to room temperature, were added 2.0 mL of toluene, 0.04 g of 2,6-difluorophenylboronic acid, 2.4 mg of palladium acetate and 2.2 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl and the resulting mixture was heated to reflux under nitrogen atmosphere for 1 hour. A saturated sodium hydrogen carbonate aqueous solution and ethyl acetate were added after the reaction mixture was cooled to room temperature. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=20:1] to obtain 31 mg of tert-butyl 2-(benzamido)-4-(2,6-difluorophenyl)benzoate as white solid.

Provenance & Evidence