2-(N-monomethylamino)-5-iodopyridine (99, 1.00 g, 4.27 mmol), potassium carbonate (2.95 g, 21.36 mmol) and iodomethane (145 mg, 8.546 mmol) were dissolved in dimethylacetamide (30 mL). The reaction mixture was heated at 90°C for 24 hours. Upon completion of the reaction, the reaction was terminated by the addition of water. The organic phase was extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography to afford 2-(N,N-dimethylamino)-5-iodopyridine (100, 603 mg, 57%).1H NMR (400 MHz, CDCl3) δ 3.08 (s, 6H), 6.34 (d, J = 8.4 Hz, 1H), 7.60 (dd, J = 8.8, 2.4 Hz, 1H), 8.27 (d, J = 2.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 38.1, 105.9, 107.1, 139.2, 148.3, 157.7.
