反应详情

温度

90 °C

A 100-mL single-neck round-bottomed flask equipped with a reflux condenser was charged with 1,4-dioxane (40 mL), 193e (800 mg, 3.6 mmol), 2-bromo-4-chloronicotinaldehyde (2.8 g, 12.6 mmol), and potassium carbonate (1.2 g, 8.4 mmol). After bubbling nitrogen through the resulting mixture for 30 minutes, copper(I) iodide (800 mg, 4.2 mmol) and 4,7-dimethoxy-1,10-phenanthroline (1.0 g, 4.2 mmol) were added, and the reaction mixture was heated at 90° C. for 12 h. After this time the reaction was cooled to room temperature and filtered. The filtrate was partitioned between methylene chloride (60 mL) and water (40 mL). The aqueous layer was separated and extracted with methylene chloride (3×40 mL). 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 by silica-gel column chromatography eluting with 1:1 ethyl acetate/petroleum ether to afford 193f as a brown solid (513 mg, yield 37%). MS-ESI: [M+H]+ 329.1.

1. customA 100-mL single-neck round-bottomed flask equipped with a reflux condenser
2. customAfter bubbling nitrogen through the resulting mixture for 30 minutes
3. temperatureAfter this time the reaction was cooled to room temperature
4. filtrationfiltered
5. customThe filtrate was partitioned between methylene chloride (60 mL) and water (40 mL)
6. customThe aqueous layer was separated
7. extractionextracted with methylene chloride (3×40 mL)
8. washThe combined organic layer was washed with brine (30 mL)
9. dry with materialdried over sodium sulfate
10. customThe drying agent was removed by filtration
11. concentrationthe filtrate was concentrated under reduced pressure
12. customThe residue was purified by silica-gel column chromatography
13. washeluting with 1:1 ethyl acetate/petroleum ether