反应详情

温度

0 °C

6-Fluoro-2-(2-methoxyvinyl)-8-(triisopropylsilyloxy)quinoline (2.5 g, 6.6 mmol) was dissolved in THF (10.3 mL) and water (2.6 mL) and cooled to 0° C. The solution was treated dropwise with a solution of freshly recrystallized N-bromosuccinimide (1.24 g, 6.99 mmol) dissolved in THF (7 mL) and water (1.75 mL). The reaction was stirred at 0° C. for 20 minutes then warmed and stirred at ambient temperature for 2.5 hours. The reaction was treated with 4-(2-methoxyethoxy)pyridin-2-amine (1.12 g, 6.65 mmol) and the mixture was heated to reflux overnight. The mixture was cooled and solids formed in the flask. Chloroform (50 mL), ethyl acetate (300 mL), and water (50 mL) were added to disperse the solids and the undissolved solids were collected by filtration and washed with ethyl acetate and water, then air-dried, (1.2 g). MS APCI (+) m/z 354.1 (M+1) detected.

1. temperaturethen warmed
2. stirringstirred at ambient temperature for 2.5 hours
3. temperaturethe mixture was heated
4. temperatureto reflux overnight
5. temperatureThe mixture was cooled
6. customsolids formed in the flask
7. additionto disperse the solids
8. filtrationthe undissolved solids were collected by filtration
9. washwashed with ethyl acetate and water
10. customair-dried