反应详情

温度

100 °C

A 50-mL round-bottomed flask equipped with a reflux condenser was charged with 1-methyl-3-(2-methylpyrimidin-4-ylamino)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one 213b (510 mg, 1.5 mmol), 4-chloro-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridine-3-carbaldehyde 108a (343 mg, 1.0 mmol), K3PO4 (424 mg, 2.0 mmol), sodium acetate (272 mg, 2.0 mmol), 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) (40 mg, 0.044 mmol), acetonitrile (20 mL), and water (0.5 mL). After bubbling nitrogen through the mixture for 30 minutes, it was was heated at 100° C. under N2 protection for 2 h. Analysis of the reaction mixture by LCMS showed complete conversion to the desired product. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was diluted with dichloromethane (30 mL) and water (30 mL). The aqueous layer was separated and extracted with dichloromethane (3×20 mL). The combined organic layer 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 179a (300 mg, 57%) as a yellow solid. MS-ESI: [M+H]+ 524

1. customA 50-mL round-bottomed flask equipped with a reflux condenser
2. customAfter bubbling nitrogen through the mixture for 30 minutes
3. temperatureThe reaction mixture was cooled to room temperature
4. filtrationfiltered
5. concentrationThe filtrate was concentrated under reduced pressure
6. additionThe residue was diluted with dichloromethane (30 mL) and water (30 mL)
7. customThe aqueous layer was separated
8. extractionextracted with dichloromethane (3×20 mL)
9. dry with materialThe combined organic layer was dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. customThe dark residue was purified by silica-gel column chromatography
13. washeluting with dichloromethane/methanol (80/1 to 30/1)