反应详情

Bromothienopyridine 50 (1.22 g, 3.30 mmol), N,N-dimethyl-3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yloxy)propan-1-amine (1.15 g, 3.76 mmol), and tetrakis(triphenylphosphine)palladium (0.14 g, 0.12 mmol) were dissolved in dry DME (100 mL). Cesium fluoride (1.51 g, 10.0 mmol) and sodium bicarbonate (0.81 g, 9.6 mmol) were dissolved in water (5 ml each) and added to the reaction mixture, which was degassed with a stream of N2, then heated to reflux for 4 h, cooled, and concentrated. The residue was partitioned between ethyl acetate and water. The organic phase was collected, washed with brine, dried (anhydrous MgSO4), filtered, and concentrated. The resulting orange solid was triturated with ether to provide 379 (1.12 g, 75% yield). LRMS (M+H): 469.2.

1. additionadded to the reaction mixture, which
2. customwas degassed with a stream of N2
3. temperatureheated
4. temperatureto reflux for 4 h
5. temperaturecooled
6. concentrationconcentrated
7. customThe residue was partitioned between ethyl acetate and water
8. customThe organic phase was collected
9. washwashed with brine
10. dry with materialdried (anhydrous MgSO4)
11. filtrationfiltered
12. concentrationconcentrated
13. customThe resulting orange solid was triturated with ether