76053-45-7

GENERAL METHOD: 2-methoxy-5-phenylpyridine (9.19 mmol) was combined with pyridine hydrochloride (10.55 g, 91.9 mmol) in a 100 mL round bottom flask and heated with continuous stirring for 20 minutes at 160°C in an oil bath. After completion of the reaction, the mixture was cooled to room temperature. Subsequently, saturated sodium chloride solution (40 mL) and deionized water (20 mL) were added for dilution. The precipitated white solid was collected by filtration and dissolved in ethyl acetate. The resulting solution was filtered through a short silica gel column and washed well with ethyl acetate until thin layer chromatography (TLC) detection showed complete conversion of the raw material to the product.

[1] Tetrahedron, 2014, vol. 70, # 45, p. 8624 - 8635
[2] Patent: US2009/318455, 2009, A1. Location in patent: Page/Page column 67; 83
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 23, p. 10584 - 10600