220939-72-0

31270-80-1

36953-42-1

220939-72-0

Example 543A Synthesis of 3-bromo-4-chlorofuro[3,2-c]pyridine: 4-Chlorofuro[3,2-c]pyridine (commercially available, 10.60 g, 69 mmol) was dissolved in carbon tetrachloride (135 mL) and the solution was cooled to -15°C. Bromine (12.13 g, 80 mmol) was added dropwise to the cooled solution over 15 minutes. After addition, the reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in methanol (250 mL), followed by the addition of 20% aqueous sodium hydroxide (35 mL) and continued stirring for 1 hour at room temperature. Methanol was again removed by reduced pressure distillation and the residue was partitioned between water (100 mL) and dichloromethane (50 mL). The organic layers were combined and dried with anhydrous magnesium sulfate. Finally, the solvent was removed by reduced pressure distillation to afford 3-bromo-4-chlorofuro[3,2-c]pyridine 15.45 g (96% yield) as a solid. Mass spectrum (ESI(+)) m/e 232,234 (M + H)+.