Dimethylformamide → HCID 86617421, compound

Participants

Reaction Conditions

Reaction Steps

After [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II)-dichloromethane adduct (82 mg, 0.1 mmol), 1,1′-bis(diphenylphosphino)ferrocene (166 mg, 0.3 mmol) and cesium carbonate (460 mg, 3 mmol) were added to a solution of N-(3-iodophenyl)-N-methylmethanesulfonamide (310 mg, 1 mmol) and tert-butyl 2-hydroxy-6-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}-3-(trifluoromethyl)benzoate (494 mg, 1 mmol) obtained in Example (22-4) in 1,4-dioxane (5 ml) and the mixture was stirred under heating at 60° C. for 4 hours, the mixture was left to stand at room temperature overnight. N,N-dimethylformamide (5 ml) was added to the reaction mixture and the mixture was stirred under heating at 70° C. for 9 hour and left to stand at room temperature for one week. The reaction mixture was poured into water and extracted with ethyl acetate (twice). The organic layer was successively washed with water and a saturated aqueous NaCl solution (twice) and dried with anhydrous magnesium sulfate. After the residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=3/1), recrystallization was carried out using tetrahydrofuran and diisopropyl ether to give the title compound as a grayish white crystal (115 mg, yield: 21%).

Provenance & Evidence