1,2-Dimethoxyethane → 8-Ethenyl-7-fluoro-2-(methoxy)-1,5-naphthyridine

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To a solution of 8-bromo-7-fluoro-2-(methyloxy)-1,5-naphthyridine (2.0 g, 7.81 mmol), potassium carbonate (1.08 g, 7.81 mmol), tetrakis-triphenylphosphine (90 mg, 0.08 mmol) in DME (60 mL) and H2O (20 mL) was added 2,4,6-trivinylcycloborane-pyridine complex (0.94 g, 3.91 mmol). After stirring for 10 h at 85° C. the reaction contents were concentrated and the product purified by chromatography (silica, 25% EtOAc in hexane) to give the title compound as a low melting solid (1.43 g, 90%): MS (ES) m/z 206 (M+H)+.

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