반응 #821729

반응 방정식

5-bromo-6-fluoro-2-methylquinoline

1,1-dimethylethyl 1-piperazinecarboxylate

bis(diphenylphosphino)-1,1′-binaphthyl

cesium carbonate

→

title compound

수율 65.8%

1,1-dimethylethyl 4-(6-fluoro-2-methyl-5-quinolinyl)-1-piperazinecarboxylate

수율 65.8%

용매

toluene

반응 조건

후처리

1. 1
   온도The mixture was cooled to room temperature
2. 2
   기타partitioned between ethyl acetate and brine
3. 3
   건조The organic layer was dried over sodium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated
6. 6
   기타This crude product was purified by flash chromatography [SiO2; DCM-MeOH (99:1)→(90:10)]

실험 절차

A mixture of 5-bromo-6-fluoro-2-methylquinoline (Chem. Pharm. Bull., 1989, 37(8), 2103-8, 0.285 g), 1,1-dimethylethyl 1-piperazinecarboxylate (0.265 g, 1.2 equiv.), Pd(OA)2 (15 mol %, 0.04 g), bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, 30 mol %, 0.221 g), cesium carbonate (1.5 equiv. 0.580 g) and toluene (3.5 mL) were stirred at 120° C. for 20 h in a sealed tube. The mixture was cooled to room temperature and partitioned between ethyl acetate and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. This crude product was purified by flash chromatography [SiO2; DCM-MeOH (99:1)→(90:10)] to afford the title compound as colourless solid (0.270 g, 65% yield).

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