反应详情

温度

80 °C

To a solution of methyl 5′,6-dichloro-3,3′-bipyridine-5-carboxylate (12-2, 7.6 g, 26.8 mmol, 1.0 equiv) in dimethylformamide (107 mL) was added 2-tri-n-butylstannylpyridine (13.8 g, 37.6 mmol, 1.4 equiv), cesium fluoride (12.2 g, 81.0 mmol, 3.0 equiv), copper (I) iodide (1.0 g, 5.4 mmol, 0.2 equiv), and tetrakis(triphenylphosphine)palladium(0) (3.1 g, 2.7 mmol, 0.1 equiv) and the system was heated to 80° C. for 2 h. The reaction mixture was cooled and diluted with ethyl acetate (300 mL) and the reaction mixture was filtered through a pad of celite. The reaction mixture was washed with water (3×100 mL) and brine (1×100 mL), dried over magnesium sulfate and concentrated. The residue was purified via normal phase chromatography (10 to 100% EtOAc in hexanes, silica) followed by chiral normal phase chromatography (Chiracel OD, 10 cm column, hexanes:IPA [1:1], flow rate 150 mL/min) to afford the desired product (12-3) as a white solid after concentration. ESI+MS [M+H]+ C17H12ClN3O2 calc'd 326.1. found 326.0.

1. temperatureThe reaction mixture was cooled
2. filtrationthe reaction mixture was filtered through a pad of celite
3. washThe reaction mixture was washed with water (3×100 mL) and brine (1×100 mL)
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated
6. customThe residue was purified via normal phase chromatography (10 to 100% EtOAc in hexanes, silica)