反应详情

温度

95 °C

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).

1. customcap tube
2. customArgon was bubbled through the reaction mixture, which
3. customwas then sealed
4. additionThe reaction mixture was diluted with water
5. extractionextracted with ethyl acetate
6. dry with materialThe organic layer was dried over sodium sulfate
7. concentrationconcentrated to a red solid, which
8. customwas purified by chromatography on silica (EtOAc 0 to 40% in hexanes)