[Br:1][C:2]1[C:3]([CH2:10][OH:11])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[CH3:21][O:22][CH2:23]Cl.CO>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH2:10][O:11][CH2:21][O:22][CH3:23])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1
A solution of 3-bromo-2-hydroxymethyl-6-methoxypyridine (10.6 g, 48.6 mmol) synthesized by the method described in Organic & Biomolecular Chemistry 1 (16) 2865-2876 (2003) in methylene chloride (150 mL) was successively added dropwise with diisopropylethylamine (31.4 g, 243 mmol) and chloromethyl methyl ether (13.3 g, 165 mmol) under ice cooling. The mixture was warmed to room temperature, stirred for 16 hours, and then added with methanol (30 mL), and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1→20:1) to obtain 3-bromo-6-methoxy-2-(methoxymethyloxy)methylpyridine (12.1 g, 95%) as pale yellow oil.
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