反应详情

温度

95 °C

A 25-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 327e (158 mg, 0.40 mmol), {3-[(acetyloxy)methyl]-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-4-yl}boronic acid 199e (159 mg, 0.40 mmol), K3PO4 (170 mg, 0.80 mmol), sodium acetate (66 mg, 0.80 mmol), Pd(dppf)Cl2 (15 mg, 0.020 mmol), and acetonitrile/water (7/0.5 mL). After three cycles of vacuum/N2 flush, the mixture was heated at 95° C. for 1 h. LCMS analysis showed complete conversion to the desired product. The reaction mixture was cooled to room temperature, and diluted with dichloromethane (50 mL) and water (30 mL). The water layer was extracted with dichloromethane (2×30 mL). The combined organic extract was dried over Na2SO4, filtered, and concentrated under reduced pressure. The dark residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (80:1 to 30:1) to afford 327f (120 mg, 45%) as a yellow solid. MS-ESI: [M+H]+ 668.8

1. customA 25-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
2. customAfter three cycles of vacuum/N2 flush
3. temperatureThe reaction mixture was cooled to room temperature
4. additiondiluted with dichloromethane (50 mL) and water (30 mL)
5. extractionThe water layer was extracted with dichloromethane (2×30 mL)
6. extractionThe combined organic extract
7. dry with materialwas dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe dark residue was purified by silica-gel column chromatography
11. washeluting with dichloromethane/methanol (80:1 to 30:1)