反应详情

温度

100 °C

A mixture of N-(5-bromo-pyrazin-2-yl)-2,2-dimethyl-propionamide (29.67 g, 114.9421 mmol), dichloro[1,1′-bis(diphenylphosphino)ferro-cene]palladium(II) dichloromethane adduct (0.95 g, 1.1633 mmol), triethylamine (17.6 mL, 126.2733 mmol), and potassium vinyltrifluoroborate (19.25 g, 143.7103 mmol) in ethanol (245 mL) was heated at 100° C. for 90 min. At this time, the reaction mixture was allowed to cool to 25° C. and then was concentrated in vacuo. The resulting orange slurry was diluted with methylene chloride (200 mL). The organic layer was washed with a 1N aqueous hydrochloric acid solution (2×200 mL), a saturated aqueous sodium bicarbonate solution (1×200 mL), and a saturated aqueous sodium chloride solution (1×200 mL). The combined aqueous layers were back-extrated with methylene chloride (1×200 mL). The combined organic layers were dried over magnesium chloride and decolorizing carbon, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 75S, Silica, 100% hexanes to 10% ethyl acetate/hexanes) afforded 2,2-dimethyl-N-(5-vinyl-pyrazin-2-yl)-propionamide (21.64 g, 92%) as an off-white solid: mp 80.4–81.8° C.; EI-HRMS m/e calcd for C11H15N3O (M+) 205.1215, found 205.1214.

1. temperatureto cool to 25° C.
2. concentrationwas concentrated in vacuo
3. additionThe resulting orange slurry was diluted with methylene chloride (200 mL)
4. washThe organic layer was washed with a 1N aqueous hydrochloric acid solution (2×200 mL)
5. dry with materialThe combined organic layers were dried over magnesium chloride
6. filtrationfiltered
7. concentrationconcentrated in vacuo