The general procedure for the synthesis of 3-(3-bromophenyl)pyridine from 1-bromo-3-iodobenzene and pyridine-3-boronic acid was as follows: 1-bromo-3-iodobenzene (1.118 g, 3.95 mmol) and pyridine-3-boronic acid (0.559 g, 4.54 mmol) were added to a 100 mL three-necked round-bottomed flask. Dioxane (20 mL) and 2N K2CO3 aqueous solution (20 mL) were added to the flask. The reaction mixture was stirred and degassed with argon for 30 minutes. Subsequently, tetrakis(triphenylphosphine)palladium (50 mg, 0.04 mmol, 1 mol%) was added under argon protection. The reaction mixture was heated to 100 °C and stirred overnight. Upon completion of the reaction, the solvent was removed by rotary evaporation. The residue was suspended in a solvent mixture of water (50 mL) and dichloromethane (50 mL). The organic layer was separated and washed with brine (50 mL x 3). The organic layer was dried with anhydrous Na2SO4 and after filtration to remove the desiccant, it was concentrated to give about 0.92 g of 3-(3-bromophenyl)pyridine in 100% yield. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.85 (s, 1H), 8.65 (d, 1H), 7.87 (d, 1H), 7.75 (s, 1H), 7.57-7.52 (m, 2H), 7.41-7.35 (m, 2H).
