反应详情

温度

90 °C

A degassed mixture of N-(5-bromo-4-(2,6-dichlorophenylthio)pyridin-2-yl)-4-methylthiazol-2-amine (1.18 g, 2.66 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1.35 g, 5.32 mmol), Pd(OAc)2 (60 mg, 0.27 mmol), tricyclopentylphosphine (93 mg. 0.40 mmol) and cesium fluoride (3.64 g, 23.9 mmol) in acetonitrile is heated at 90° C. for 5 hours. The reaction mixture is cooled and partitioned between ether and water. The crude product is dissolved in THF. N-morpholine N-oxide (1.40 g, 12.0 mmol) is added and the reaction mixture is heated at reflux for 12 hours. The reaction mixture is cooled and partitioned between ether and water. The organic layer is washed with water and brine, dried and concentrated. The residue is purified by silica gel chromatography, eluting with 10-20% EtOAc in hexanes to afford 4-(2,6-dichlorophenylthio)-6-(4-methylthiazol-2-ylamino)pyridin-3-ol.

1. temperatureThe reaction mixture is cooled
2. custompartitioned between ether and water
3. dissolutionThe crude product is dissolved in THF
4. temperaturethe reaction mixture is heated
5. temperatureat reflux for 12 hours
6. temperatureThe reaction mixture is cooled
7. custompartitioned between ether and water
8. washThe organic layer is washed with water and brine
9. customdried
10. concentrationconcentrated
11. customThe residue is purified by silica gel chromatography
12. washeluting with 10-20% EtOAc in hexanes