反应详情

温度

100 °C

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 1,4-dioxane (60 mL), 101c (1.9 g, 6.0 mmol), 101g (400 mg, 2.0 mmol), and cesium carbonate (1.3 g, 4.0 mmol). After bubbling nitrogen through the resulting mixture for 30 minutes, Xantphos (120 mg, 0.2 mmol) and tris(dibenzylideneacetone)dipalladium(0) (180 mg, 0.2 mmol) were added, and the reaction mixture was heated at 100° C. for 12 h. After this time the reaction was cooled to room temperature, partitioned between ethyl acetate (40 mL) and water (40 mL), and filtered. The aqueous layer was separated and extracted with ethyl acetate (70 mL×3). The combined organic layer was washed with brine (30 mL) and dried over sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified on flash column eluting with 2:1 PE/EA to afford 101h (421 mg, 46%) as yellow solid. MS: [M+H]+ 435. 1H NMR (500 MHz, MeOD) δ 7.52-7.50 (m, 1H), 7.20-7.23 (m, 1H), 6.14 (s, 1H), 5.10-5.20 (m, 2H), 4.06-4.12 (m, 1H), 3.92-3.97 (m, 1H), 3.83-3.88 (m, 1H), 3.75-3.79 (m, 1H), 3.03-3.10 (m, 1H), 2.94-2.99 (m, 1H), 2.75-2.83 (m, 2H), 2.00-2.05 (m, 5H), 1.83-1.88 (m, 2H)

1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
2. temperaturereflux condenser
3. customAfter bubbling nitrogen through the resulting mixture for 30 minutes
4. temperatureAfter this time the reaction was cooled to room temperature
5. custompartitioned between ethyl acetate (40 mL) and water (40 mL)
6. filtrationfiltered
7. customThe aqueous layer was separated
8. extractionextracted with ethyl acetate (70 mL×3)
9. washThe combined organic layer was washed with brine (30 mL)
10. dry with materialdried over sodium sulfate
11. customThe drying agent was removed by filtration
12. concentrationthe filtrate was concentrated under reduced pressure
13. customThe residue was purified on flash column
14. washeluting with 2:1 PE/EA