Synthesis
Methyl 2-chloro-6-methylpyridine-4-carboxylate (15.0 g, 80.8 mmol) was added with 10% palladium carbon catalyst (50% water, 5.00 g) and triethylamine (22.5 mL, 162 mmol) in N,N-dimethylformamide (200 mL). The reaction was stirred for 15 hours at room temperature under hydrogen atmosphere. After completion of the reaction, the catalyst was removed by filtration and the solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography with the eluent ethyl acetate:methanol (100:0 to 50:1) to afford methyl 2-methylpyridine-4-carboxylate (14.8 g, 61% yield) as an oil.1H NMR (CDCl3) δ: 2.64 (3H, s), 3.95 (3H, s), 7.64 (1H, dd, J = 5.2, 0.8 Hz), 7.72 (1H, s), 8.65 (1H, d, J = 4.7 Hz).
References
[1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 3, p. 647 - 660
[2] Patent: US5962458, 1999, A
[3] Patent: US6362336, 2002, B1. Location in patent: Example 63
[4] Helvetica Chimica Acta, 1955, vol. 38, p. 1046,1058
[5] Bulletin de la Societe Chimique de France, 1958, p. 687,691
