반응 #44108

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N,N-Diisopropylethylamine

2-methyl-5-(1-piperazinyl)-6-fluoro quinoline

2-(3-nitrophenyl)ethyl methanesulfonate

→

title compound

수율 42.0%

6-Fluoro-2-methyl-5-{4-[2-(3-nitrophenyl)ethyl]-1-piperazinyl}quinoline

수율 42.0%

용매

dimethylformamide

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후처리

1. 1
   농축The dark solution was concentrated under reduced pressure
2. 2
   workup.ADDITIONdiluted with water (3 mL) and brine (1 mL)
3. 3
   추출extracted into ethyl acetate (3×3 mL)
4. 4
   건조dried over sodium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The crude was purified by flash chromatography on silica gel
7. 7
   세척eluting with a gradient from dichloromethane to dichloromethane-methanol (98:2)

실험 절차

N,N-Diisopropylethylamine (0.15 mL; 3 eq) was added to a solution of 2-methyl-5-(1-piperazinyl)-6-fluoro quinoline (0.075 g; 1 eq) and 2-(3-nitrophenyl)ethyl methanesulfonate (D4) (0.08; 1.1 eq) in dimethylformamide (3.0 mL). The reaction mixture was heated to 100° C. for 10 hours. The dark solution was concentrated under reduced pressure, diluted with water (3 mL) and brine (1 mL) and extracted into ethyl acetate (3×3 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The crude was purified by flash chromatography on silica gel, eluting with a gradient from dichloromethane to dichloromethane-methanol (98:2) affording the title compound in 42% yield (0.05 g).

출처