反应详情

温度

50 °C

To a solution of 2-bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (3.1 g, 8.8 mmol, Example #1, Step B), PdCl2(dppf)•DCM (0.719 g, 0.880 mmol) and (E)-styrylboronic acid (2.60 g, 17.6 mmol) in THF (3 mL) and water (2 mL) was added Na2CO3 (2.33 g, 22.0 mmol). The reaction mixture was degassed with argon for about 5 min. The reaction mixture was heated at about 50° C. After about 24 h, additional PdCl2(dppf)•DCM (0.719 g, 0.880 mmol), (E)-styrylboronic acid (2.60 g, 17.6 mmol) and Na2CO3 (2.33 g, 22.0 mmol) were added to the reaction mixture. After heating at about 50° C. for about 48 h, the reaction mixture was cooled to ambient temperature and diluted with DCM (200 mL) and water (200 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and coned under reduced pressure. Purification by chromatography over silica gel eluting with a gradient of 20-60% EtOAc in heptane containing 5% DCM provided (E)-2-styryl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine as a yellow solid (1.2 g, 36%): LC/MS (Table 1, Method a) Rt=2.99 min; MS m/z: 376 (M+H)+.

1. customThe reaction mixture was degassed with argon for about 5 min
2. temperatureAfter heating at about 50° C. for about 48 h
3. temperaturethe reaction mixture was cooled to ambient temperature
4. customThe organic layer was separated
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. customPurification by chromatography over silica gel eluting with a gradient of 20-60% EtOAc in heptane containing 5% DCM