153034-80-1

113975-22-7

74-88-4

153034-80-1

General procedure for the synthesis of 2-fluoro-3-methyl-4-iodopyridine from 2-fluoro-3-iodopyridine and iodomethane: A THF solution of 2-fluoro-3-iodopyridine (30 g, 135 mmol) was slowly added to a THF solution of LDA (68 mL, 135 mmol) in THF (100 mL) at -78 °C under nitrogen protection, maintaining the temperature at -78 °C and stirring for 1 hour. Subsequently, iodomethane (25 mL, 405 mmol) was added to the reaction system and stirring was continued at -78 °C for 30 min. Upon completion of the reaction, the reaction was quenched with saturated aqueous NaHCO3 solution and NaHCO3 solution at -78 °C was added. The reaction mixture was extracted with ether and the combined organic phases were dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent ratio petroleum ether:EtOAc = 4:1) to afford 2-fluoro-3-methyl-4-iodopyridine as a brown solid (22 g, 69% yield).MS (ES+) analysis showed that the theoretical value of C6H5FIN was 237 and the measured value was 238 [M + H]+ .