反应详情

温度

125 °C

4-[5-(3-Amino-5-nitrophenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one (482 mg, 1.446 mmol), XantPhos (251 mg, 0.434 mmol), cesium carbonate (942 mg, 2.89 mmol), palladium(II) acetate (64.9 mg, 0.289 mmol), dioxane (10 mL) and 2-chloro-4-(trifluoromethyl)pyrimidine (0.174 mL, 1.446 mmol) were successively added in a sealable reaction tube under nitrogen. The tube was sealed and the mixture was stirred at 125° C. for 5 hours. The reaction mixture was cooled to room temperature, partitioned between 25% aqueous ammonium acetate and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate and three times with 2-methyltetrahydrofuran. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Purification via CombiFlash (ethanol/dichloromethane) afforded 4-[5-(3-nitro-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one as an amber gum. MS APCI: [M+H]+ m/z 480.1.

1. customThe tube was sealed
2. temperatureThe reaction mixture was cooled to room temperature
3. custompartitioned between 25% aqueous ammonium acetate and ethyl acetate
4. extractionThe aqueous layer was extracted twice with ethyl acetate and three times with 2-methyltetrahydrofuran
5. washThe combined organic layers were washed with brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customPurification via CombiFlash (ethanol/dichloromethane)