反应详情

温度

90 °C

[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid (R)-1-phenyl-ethyl ester (39 g, 97.2 mmol), [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester (31 g, 107 mmol), and sodium bicarbonate (32.6 g, 389 mmol) were combined in 3:1 DME:H2O (500 mL), and the mixture was purged with N2 for 15 minutes. (1,1′-Bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (2.13 g, 2.91 mmol) was added, and the reaction was purged with N2 for an additional 10 minutes and then stirred at 90° C. overnight. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with H2O, dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (EtOAc/hexane gradient) to give the title compound.

1. customH2O (500 mL), and the mixture was purged with N2 for 15 minutes
2. customthe reaction was purged with N2 for an additional 10 minutes
3. customThe mixture was partitioned between EtOAc and H2O
4. extractionthe aqueous layer was extracted with EtOAc
5. washThe combined organic layers were washed with H2O
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customthe residue was purified by silica gel chromatography (EtOAc/hexane gradient)