반응 #57147

반응 방정식

N-{4-[4-bromo-1-(tetrahydro-2-furanylmethyl)-1H-pyrazol-3-yl]phenyl}-N′-phenylurea

1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

sodium bicarbonate

→

title compound

수율 11.0%

N-phenyl-N′-{4-[4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-(tetrahydro-2-furanylmethyl)-1H-pyrazol-3-yl]phenyl}urea

수율 11.0%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   온도The solution was cooled to room temperature
2. 2
   여과filtered though Celite
3. 3
   농축concentrated in vacuo
4. 4
   workup.DISSOLUTIONThe residue was dissolved in methanol (5 mL)
5. 5
   workup.STIRRING6.0N aqueous sodium hydroxide (1 mL) and stirred at 70° C. for 6 h
6. 6
   농축The reaction mixture was concentrated in vacuo
7. 7
   workup.DISSOLUTIONdissolved in water (10 mL)
8. 8
   추출extracted with ethyl acetate (3×10 mL)
9. 9
   건조The combined organic extracts were dried over magnesium sulfate
10. 10
    농축concentrated in vacuo
11. 11
    기타Purification of the residue by Gilson reverse phase HPLC

실험 절차

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

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