反应详情

温度

110 °C

A suspension of tert-butyl 4-(5,6-dichloropyridin-3-yl)-3-methylbenzoate (Step A, 650 mg, 1.92 mmol), potassium methyltrifluoroborate (234 mg, 1.92 mmol), Cs2CO3 (1.88 g, 5.77 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (157 mg, 0.192 mmol), dioxane (4 mL) and water (0.25 mL) was flushed with nitrogen and stirred at 110° C. for 2 hours. After cooling down, the mixture was filtered over celite. The filter cake was washed with ethyl acetate and further diluted with ethyl acetate and water. After separating the layers, the organic was washed with brine. The organic layer was dried over sodium sulfate, filtered and the filtrate was concentrated. The crude isolate was purified by silica gel chromatography (0 to 80% ethyl acetate/hexane) to give the titled compound as a white solid. 1H NMR (500 MHz, CDCl3): δ 8.38 (d, J=1.9 Hz, 1H), 7.94 (s, 1H), 7.90 (d, J=8.0 Hz, 1H), 7.63 (d, J=1.8 Hz, 1H), 7.27 (d, J=7.9 Hz, 1H), 2.7 (s, 3H), 2.35 (s, 3H), 1.64 (s, 9H).

1. customwas flushed with nitrogen
2. temperatureAfter cooling down
3. filtrationthe mixture was filtered over celite
4. washThe filter cake was washed with ethyl acetate
5. additionfurther diluted with ethyl acetate and water
6. customAfter separating the layers
7. washthe organic was washed with brine
8. dry with materialThe organic layer was dried over sodium sulfate
9. filtrationfiltered
10. concentrationthe filtrate was concentrated
11. customThe crude isolate
12. customwas purified by silica gel chromatography (0 to 80% ethyl acetate/hexane)