Pyridine → 8-Bromo-1,6-naphthyridine

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To a stirred solution of [1,6]-naphthyridine (4.73 g, 36.4 mmol) in CCl4 (200 25 mL) was added Br2 (2.25 mL, 43.7 mmol) in CCl4 (35 mL) dropwise via an addition funnel. The resulting solution was heated at reflux for 1 hour. Pyridine (2.94 mL, 36.4 mmol) in CCl4 (30 mL) was added dropwise to the refluxing solution, and the mixture was refluxed overnight. The cooled reaction mixture was filtered, and the solids were digested with 1 M NaOH (200 mL) for 1 hour. The basic solution was extracted into CH2Cl2 (2×200 mL), and the organic fractions were combined, dried over Na2SO4 and concentrated. The resulting oil was purified by column chromatography (10% EtOAc/CH2Cl2) affording 2.03 g (27%) of the title compound as yellow crystals: mp 79-81° C.

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