反应详情

温度

100 °C

To a solution of crude 3-bromo-2-chloro-4-iodopyridine (10.0 g, 31.41 mmol) in toluene (120 mL) at room temperature under argon was added 4-chlorophenylboronic acid (5.8 g, 37.1 mmol), tetrakis(triphenylphosphine)palladium (2.2 g, 1.9 mmol), and a solution of Na2CO3 (6.6 g, 62.3 mmol) in water (20 mL). The resulting suspension was stirred and heated at 100° C. under argon for 2.5 h. After the reaction mixture was cooled to room temperature, water (120 mL) and EtOAc (150 mL) were added. The layers were separated. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel column eluting with 7% ethyl acetate-hexanes) to isolate 3.7 g of the title compound as a white solid. HPLC/MS: retention time=3.78 min, [M+H]+=302. 1H NMR (CDCl3, 500 MHz): δ 8.35 (d, J=5.0 Hz, 1H), 7.46 (d, J=10.0 Hz, 2H), 7.34 (d, J=10.0 Hz, 2H), 7.14 (d, J=5.0 Hz, 1H).

1. temperatureAfter the reaction mixture was cooled to room temperature
2. customThe layers were separated
3. dry with materialThe organic layer was dried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customThe crude product was purified by flash chromatography (silica gel column eluting with 7% ethyl acetate-hexanes)