To a solution of 2-(2-methyl-tetrazolyl)-5-bromopyridine (1.00 g, 4.17 mmol) in dry degassed 1,4-dioxane (15 mL) was added bis(pinacolato)diboron (1.27 g, 5.00 mmol), potassium acetate (1.35 g, 13.75 mmol), and Pd(dppf)Cl2 (0.26 g, 0.35 mmol). The reaction mixture was placed in a sealed tube under argon protection and heated and stirred at 80°C for 3 hours. Upon completion of the reaction, the mixture was rapidly filtered through a silica gel column and dichloromethane was used as eluent. The organic layer was collected, concentrated under reduced pressure and the residue was washed with hexane to afford the white solid product 2-(2-methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1.03 g, 86.3% yield). The product was characterized by 1H-NMR (400 MHz, CDCl3): δ 9.14 (s, 1H), 8.30 (m, 2H), 4.48 (s, 3H), 1.38 (s, 12H).
