反应详情

To a mixture of the triflate 377 (450 mg, 1.84 mmol), bis(pinacolato)diboron (477 mg, 2.02 mmol) and K2CO3 (541 mg, 5.52 mmol) in DME (3.7 mg), Pd(PPh3)4 (106 mg, 0.092 mmol) was added in one portion and the system was heated to reflux for 2 h under N2. The reaction mixture was cooled and filtered. To the filtrate containing the intermediate 378 were added bromide 42 (435 mg, 1.84 mmol, scheme 8), CsF (838 mg, 5.52 mmol), NaHCO3 (463 mg, 5.52 mmol) and water (0.8 mL), and the mixture was heated to reflux for additional 2 h. It was then diluted with water and extracted with DCM; the organic solution was extracted with 1N HCl, the aqueous phase was basified to pH˜11 by addition of 2N aqueous NaOH, extracted with DCM; the extract was dried over anhydrous Na2SO4 and concentrated under reduced pressure affording 379 (279 mg, 39% yield) as a brown solid. LCMS:(M+H) 385.9.

1. additionwas added in one portion
2. temperaturethe system was heated
3. temperatureto reflux for 2 h under N2
4. temperatureThe reaction mixture was cooled
5. filtrationfiltered
6. additionTo the filtrate containing the intermediate 378
7. temperaturethe mixture was heated
8. temperatureto reflux for additional 2 h
9. extractionextracted with DCM
10. extractionthe organic solution was extracted with 1N HCl
11. additionthe aqueous phase was basified to pH˜11 by addition of 2N aqueous NaOH
12. extractionextracted with DCM
13. dry with materialthe extract was dried over anhydrous Na2SO4
14. concentrationconcentrated under reduced pressure