Water → HCID 46206782, compound

Participants

Reaction Steps

A mixed solution of N-[1,1-bis(acetoxymethyl)-3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]propyl]acetamide (867 mg) of Reference Example 9, 1-benzyloxy-4-bromo-3-fluorobenzene (674 mg), sodium hydrogen carbonate (1.01 g) and tetrakistriphenylphosphine palladium (46 mg) in 1,2-dimethoxyethane (15 mL)-water (5 mL) was stirred at 65° C. for 5 hr. The reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. To a solution of the residue in methanol (30 mL) were added palladium carbon (10%, 0.3 g) and ammonium formate (517 mg), and the mixture was stirred at room temperature for 6 hr under a nitrogen atmosphere. The reaction mixture was filtered through celite, and the solvent was evaporated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (0.56 g) as white amorphous crystals.

Provenance & Evidence