Water → 6-Bromo-2-methoxypyridin-3-amine

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A solution of 2-methoxypyridin-3-amine (39.4 g) in N,N-dimethylformamide (200 mL) was cooled to −30° C., and a solution of N-bromosuccinimide (62.1 g) in N,N-dimethylformamide (100 mL) was added dropwise. After stirring for 30 minutes, the reaction solution was poured into water and extracted with chloroform. The organic layer was sequentially washed with a saturated sodium sulfite solution, water and brine and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1) to give 6-bromo-2-methoxypyridin-3-amine as a yellow powder (51.9 g, 80%).

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