反应详情

温度

100 °C

A mixture of N-{4-[4-bromo-1-(tetrahydro-2-furanylmethyl)-1H-pyrazol-3-yl]phenyl}-N′-phenylurea (0.147 mmol), 1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (0.162 mmol), N,N-dimethylformamide (1.5 mL), saturated aqueous sodium bicarbonate (0.44 mL) and tetrakis(triphenylphosphine)palladium(0) (0.007 mmol) in a sealed tube was stirred at 100° C. for 18 hrs. The solution was cooled to room temperature, filtered though Celite and concentrated in vacuo. The residue was dissolved in methanol (5 mL) and 6.0N aqueous sodium hydroxide (1 mL) and stirred at 70° C. for 6 h. The reaction mixture was concentrated in vacuo, dissolved in water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by Gilson reverse phase HPLC afforded the title compound as a white solid (11%). ESMS [M+H]+: 479.4

1. temperatureThe solution was cooled to room temperature
2. filtrationfiltered though Celite
3. concentrationconcentrated in vacuo
4. dissolutionThe residue was dissolved in methanol (5 mL)
5. stirring6.0N aqueous sodium hydroxide (1 mL) and stirred at 70° C. for 6 h
6. concentrationThe reaction mixture was concentrated in vacuo
7. dissolutiondissolved in water (10 mL)
8. extractionextracted with ethyl acetate (3×10 mL)
9. dry with materialThe combined organic extracts were dried over magnesium sulfate
10. concentrationconcentrated in vacuo
11. customPurification of the residue by Gilson reverse phase HPLC