272-14-0

28783-18-8

General procedure for the synthesis of 3-bromothieno[3,2-c]pyridine from thieno[3,2-c]pyridine: 0.46 g of thieno[3,2-c]pyridine (10.8 mmol), 907 mg of NaHCO3 (10.8 mmol), 2.82 g of K2HPO4 (16.2 mmol) and 1.69 g of MgSO4 (14.04 mmol) were placed in a flask and 40 mL of chloroform was added. The reaction mixture was stirred under reflux conditions. 0.72 mL of bromine (14.04 mmol) was added slowly and stirring was continued overnight. Upon completion of the reaction, the cooled reaction mixture was extracted with CH2Cl2 and water, and the separated CH2Cl2 layer was dried with Na2SO4 and the solvent was evaporated. The crude product was purified by silica gel column chromatography (eluent ratio: hexane:AcOEt = 5:1 → hexane:AcOEt:2M NH3 in MeOH = 10:3:1) to give 660 mg of 3-bromothieno[3,2-c]pyridine in 29% yield. The product was characterized by mass spectrometry (m/e: 215 [M+1]) and 1H-NMR (CDCl3: δ 9.17 (m, 1H), 8.59 (m, 1H), 7.83 (d, 1H, J = 5.2 Hz), 7.52 (s, 1H) ppm).