反应详情

温度

70 °C

A mixture of methyl 3-bromo-4-(tetrahydro-2H-pyran-2-yloxy)benzoate 66.6F (0.500 g, 1.6 mmol), palladium acetate (0.036 g, 0.16 mmol), S-Phos (0.13 g, 0.32 mmol) and tripotassium phosphate (0.32 mL, 4.0 mmol) in DMF (10.00 mL, 129 mmol) and water (0.40 mL, 22 mmol) was stirred. The mixture was purged with nitrogen and placed under vacuum and the process repeated three times. Before heating, 2-methylprop-1-enylboronic acid (0.24 g, 2.4 mmol, commercially available from Synthonix, Cat. No. D3007G1) was added, and the mixture was heated to 70° C. and stirred for 23 hours. The mixture was then cooled to room temperature, diluted with brine, and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 66.20A as a colorless oil (0.460 g, 100% yield).

1. customThe mixture was purged with nitrogen
2. temperatureBefore heating
3. additionD3007G1) was added
4. stirringstirred for 23 hours
5. temperatureThe mixture was then cooled to room temperature
6. additiondiluted with brine
7. extractionextracted three times with EtOAc
8. dry with materialAfter drying over anhydrous magnesium sulfate
9. filtrationfiltering
10. customthe organic solvent was removed under reduced pressure
11. customthe product was then purified on silica gel (0-10% EtOAc in hexanes)