반응 #74678

반응 방정식

5-chloro-4-(4-chloro-2-(3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)phenoxy)-2-fluoro-N-(methoxymethyl)-N-(pyrimidin-4-yl)benzenesulfonamide

ethanol

ammonium chloride

→

colorless oil

수율 97.8%

4-{2-[3-amino-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]-4-chlorophenoxy}-5-chloro-2-fluoro-N-(methoxymethyl)-N-pyrimidin-4-ylbenzenesulfonamide

수율 97.8%

반응 조건

후처리

1. 1
   여과then filtered
2. 2
   workup.ADDITIONSaturated aqueous sodium bicarbonate was added until the pH was 9
3. 3
   농축The mixture was concentrated in vacuo
4. 4
   기타to remove the ethanol
5. 5
   workup.ADDITIONWater was added
6. 6
   추출the mixture was extracted three times with dichloromethane
7. 7
   건조The combined organic phase was dried over anhydrous sodium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated in vacuo
10. 10
    기타The residue was purified on silica gel (hexane to 100% ethyl acetate gradient)

실험 절차

To a solution of 5-chloro-4-(4-chloro-2-(3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)phenoxy)-2-fluoro-N-(methoxymethyl)-N-(pyrimidin-4-yl)benzenesulfonamide (80 mg, 0.1 mmol) in ethanol (4 mL, 70 mmol) was added saturated aqueous ammonium chloride solution (0.4 mL, 6 mmol) and iron (328 mg, 5.87 mmol). The reaction solution was heated at 80° C. for 20 minutes then filtered. Saturated aqueous sodium bicarbonate was added until the pH was 9. The mixture was concentrated in vacuo to remove the ethanol. Water was added and the mixture was extracted three times with dichloromethane. The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified on silica gel (hexane to 100% ethyl acetate gradient) to give 61 mg of a colorless oil.

출처