939430-30-5

73183-34-3

4422-32-6

939430-30-5

3-(3-bromophenyl)pyridine (14.5 g, 61.9 mmol), bis(pinacolato)diboron (18.9 g, 74.3 mmol) and potassium acetate (18.2 g, 185 mmol) were mixed in dry 1,4-dioxane (477 mL) and sprayed with nitrogen for 15 min. Subsequently, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride complex with dichloromethane (1:1) (1.52 g, 1.86 mmol) was added and nitrogen injection was continued for 10 minutes. The mixture was heated to reflux the reaction for 18 hours. After completion of the reaction, it was cooled to room temperature and the crude reaction mixture was poured onto a silica gel pad and eluted sequentially with toluene and a 1:1 solvent mixture of ethyl acetate/hexane. The filtrates were combined and concentrated by rotary evaporation to give a dark brown oil. The oily substance was purified by silica gel MPLC using a hexane solution of 10-100% ethyl acetate as eluent. The grades eluting in 30-65% hexane solution of ethyl acetate were collected, combined and concentrated by rotary evaporation and dried under high vacuum to give 3-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine (17.3 g, 99.3% yield) as an off-white solid.