3-chloro-2-[(1-methylethyl)oxy]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (D108) (1.2 g, 4.03 mmol), 3-bromo-5-chloro-1,2,4-thiadiazole (1.609 g, 8.06 mmol), tripotassium phosphate (2.57 g, 12.10 mmol) and PdCl2(dppf)-CH2Cl2 adduct (0.329 g, 0.403 mmol) were heated by Biotage Initiator to 80° C. for 1 hr. The reaction mixture was concentrated and the slurry was diluted with ethyl acetate. The resulted solution was washed with water, dried and purified by ISCO column chromatography to afford 5-(3-bromo-1,2,4-thiadiazol-5-yl)-3-chloro-2-[(1-methylethyl)oxy]pyridine (D109) (1.3 g). δH (CDCl3, 400 MHz): 1.43 (6H, d), 5.45 (1H, m), 8.21 (1H, d), 8.59 (1H, d). MS (ES): C10H9BrClN3OS requires 332.9. found 334.0 (M+H+).
