36953-42-1

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 cooled to -15°C. Bromine (12.13 g, 80 mmol) was added dropwise over 15 min. The reaction mixture was stirred at room temperature for 18 hours. Upon completion of the reaction, the solvent was removed under vacuum. The residue was dissolved in methanol (250 mL), 20% aqueous sodium hydroxide solution (35 mL) was added and stirring was continued for 1 hour at room temperature. Subsequently, methanol was removed under vacuum and the residue was partitioned between water (100 mL) and dichloromethane (50 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo 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)+.