反应详情

3-(4-{2-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-2-methylphenyl)-propionic acid methyl ester (592 mg, 1.25 mmol) is dissolved in anhydrous toluene (5 mL), degassed, and filled with nitrogen three times. Palladium tetrakis triphenyl phosphine [Pd(PPh3)4, 25 mg, 0.025 mmol] is added, and the degassing procedure is repeated. 2-tributylstannylpyridine (635 uL, 2.5 mmol) is then added via syringe and the reaction is heated to reflux. The reaction is monitored by HPLC. Upon complete consumption of starting material, the reaction is allowed to cool to room temperature and diluted with ethyl acetate. Celite is added and the mixture is filtered and rinsed with more ethyl acetate and water. The solution is further diluted with water and the two phases are separated. The organic layer is washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The pure 3-(2-Methyl-4-{2-[5-methyl-2-(4-pyridin-2-yl-phenyl)-oxazol-4-yl]-propoxy}-phenyl)-propionic acid methyl ester is obtained after column chromatography.

1. customdegassed
2. additionfilled with nitrogen three times
3. temperaturethe reaction is heated to reflux
4. customUpon complete consumption of starting material
5. additiondiluted with ethyl acetate
6. additionCelite is added
7. filtrationthe mixture is filtered
8. washrinsed with more ethyl acetate and water
9. additionThe solution is further diluted with water
10. customthe two phases are separated
11. washThe organic layer is washed with water and brine
12. dry with materialdried over anhydrous sodium sulfate
13. filtrationfiltered
14. concentrationconcentrated