反应详情

温度

90 °C

A 40-mL vial containing 5-bromo-2-(3-fluorophenyl)-4-methoxypyridine (0.420 g, 1.489 mmol), (E)-ethyl 3-(2-amino-5-(benzylthio)phenyl)acrylate (0.560 g, 1.787 mmol), Xantphos (0.172 g, 0.298 mmol), cesium carbonate (0.679 g, 2.084 mmol), and Pd2(dba)3 (0.136 g, 0.149 mmol) was flushed with N2 and charged with CPME (3 mL). After stirring overnight at 90° C., additional Pd2(dba)3 (0.136 g, 0.149 mmol) and Xantphos (0.172 g, 0.298 mmol) was added. After stirring an additional 4 h, the reaction was cooled to rt, quenched with H2O and extracted thrice with EtOAc. The organic extracts were combined, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to a brown-black oil. Column chromatography (50 g Snap Ultra column, 0% to 80% EtOAc/hept) afforded (E)-ethyl 3-(5-(benzylthio)-2-((6-(3-fluorophenyl)-4-methoxypyridin-3-yl)amino)phenyl)acrylate (0.615 g, 1.195 mmol, 80% yield) as a yellow oil. m/z (ESI) 515.2 (M+H)+.

1. customwas flushed with N2
2. additioncharged with CPME (3 mL)
3. stirringAfter stirring an additional 4 h
4. temperaturethe reaction was cooled to rt
5. customquenched with H2O
6. extractionextracted thrice with EtOAc
7. washwashed with brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo to a brown-black oil