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Synthesis of 4-chloro-3-iodoquinoline (Compound 16): 4-hydroxy-3-iodoquinoline (Compound 15, 1000 mg, 3.69 mmol) was dissolved in 25 mL of phosphorus oxychloride (POCl3). The reaction mixture was stirred at 100°C for 2 hours. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure, followed by the addition of ice water. The solid product was collected by filtration and dried under vacuum to give compound 16 as a white solid (900 mg, 85% yield).

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