General Steps:
1. 2-Chloro-6-hydroxynicotinic acid (3.00 g, 17.3 mmol) and chloroform (30 mL) were added to a 50 mL round-bottomed flask and stirred until completely dissolved.
2. Silver carbonate (11.0 g, 39.8 mmol) and methyl iodide (3.77 mL, 60.5 mmol) were added sequentially to the above solution.
3. The reaction mixture was stirred at 50 °C for 3 hours and the reaction was monitored by TLC. 4.
4. After completion of the reaction, the mixture was vacuum filtered and the filter cake was washed with chloroform.
5. The filtrate and washings were combined and concentrated under reduced pressure in a rotary evaporator to give the crude product.
6. The crude product was purified by fast column chromatography (eluent: 0-100% ethyl acetate/heptane gradient elution) and the target fraction was collected.
7. The target fraction was concentrated under pressure to afford methyl 2-chloro-6-methoxypyridine-3-carboxylate (2.42 g, 69% yield) as a white powder. 8. The product was purified by LCMS (0-100% ethyl acetate/heptane gradient elution).
8. The product was characterized by LCMS (Method D): retention time 1.13 min, m/z = 202 (M + 1).
