1,4-Dioxane → Methyl 4-(2-fluoro-5-methylpyridin-4-yl)benzoate

참여 물질

반응 조건

반응 단계

2-Fluoro-4-iodo-5-methyl-pyridine (0.90 g, 3.8 mmol), 4-carboxymethyl-phenyl boronic acid (0.72 g, 4.0 mmol), potassium phosphate (2.5 g, 11.8 mmol), and dichloro[1,1′-bis(diphenylphoshino)ferrocene]palladium (II) dichloromethane adduct (0.30 g, 0.37 mmol) were combined in a screw cap tube and 1.4-dioxane (20 mL) was added. Argon was bubbled through the reaction mixture, which was then sealed and heated to 95° C. overnight. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to a red solid, which was purified by chromatography on silica (EtOAc 0 to 40% in hexanes) to afford 4-(2-fluoro-5-methyl-pyridin-4-yl)-benzoic acid methyl ester, 0.62 g, 2.5 mmol, 66% yield. 1H NMR 500 MHz (CDCl3): 8.05 (m, 3H), 7.33 (d, 2H), 6.74 (s, 1H), 3.90 (s, 3H), 2.15 (s, 3H).

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