反应详情

温度

90 °C

To a solution of 5-(4-(2-(6-chloropyridin-2-yl)ethoxy)phenyl)isoxazol-3-ol (46.5 mg) in dimethoxyethane ethylene glycol dimethyl ether (3 ml), 18 mg of tetrakis triphenylphosphine palladium, 31 mg of 4-fluorophenylboronic acid and 0.2 ml of 2M aqueous sodium carbonate solution were added, and the reaction solution was stirred at 90° C. for 2 hours. The reaction solution was cooled, then diluted with a saturated saline solution, extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified through reversed phase medium pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid). The solvent of the resultant fraction was diluted with ethyl acetate, washed with saturated sodium bicarbonate water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., methanol/chloroform (1:9)) to afford the title compound as a brown solid.

1. temperatureThe reaction solution was cooled
2. additiondiluted with a saturated saline solution
3. extractionextracted with ethyl acetate
4. dry with materialdried over anhydrous magnesium sulfate
5. distillationThe solvent was distilled off under reduced pressure
6. customthe residue obtained
7. customwas purified through reversed phase medium pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid)
8. additionThe solvent of the resultant fraction was diluted with ethyl acetate
9. washwashed with saturated sodium bicarbonate water
10. dry with materialdried over anhydrous magnesium sulfate
11. distillationThe solvent was distilled off under reduced pressure
12. customthe residue obtained
13. customwas purified by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., methanol/chloroform (1:9))