The general procedure for the synthesis of 5-bromomethyl-2-chloropyridine using 2-chloro-5-methylpyrimidine as starting material was as follows: synthetic embodiment 25, N-[1-((2-chloropyrimidin-5-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (compound 243). 2-Chloro-5-methylpyrimidine (1.04 g, 8.13 mmol) was dissolved in 30 mL of carbon tetrachloride and N-bromosuccinimide (1.73 g, 9.75 mmol) and benzoyl peroxide (20 mg) were added. The mixture was heated to reflux for 6 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature, concentrated under reduced pressure and purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 3:1) to afford 5-bromomethyl-2-chloropyridine 641 mg (38% yield).1H-NMR (CDCl3, δ, ppm): 4.42 (2H, s), 8.66 (2H, s).
