反应详情

温度

100 °C

In a sealed tube a mixture of 7-bromo-2,8-dimethylquinoline (0.60 g, 2.54 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.06 g, 5.08 mmol), PdCl2(dppf)*dcm (0.208 g, 0.254 mmol), CsF (1.00 g, 6.61 mmol) and triethylamine (0.531 mL, 3.81 mmol) in isopropyl alcohol (17 mL) was heated at 100° C. on an oil bath for 6 hours. The mixture was cooled to ambient temperature and partitioned between water (25 mL) and ethyl acetate (50 mL). The solids were removed by filtration through a pad of Celite and washed with additional ethyl acetate. The layers were separated and the organic layer washed with brine and dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Biotage 25M; 25% ethyl acetate/hexane) to afford 2,8-dimethyl-7-(4-methyl-1H-pyrazol-1-yl)quinoline (0.60 g, 91%).

1. temperatureThe mixture was cooled to ambient temperature
2. custompartitioned between water (25 mL) and ethyl acetate (50 mL)
3. customThe solids were removed by filtration through a pad of Celite
4. washwashed with additional ethyl acetate
5. customThe layers were separated
6. washthe organic layer washed with brine
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by column chromatography (Biotage 25M; 25% ethyl acetate/hexane)