참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Cesium carbonate | HCID 10796 | — |
| 반응물 | tert-Butyl piperazine-1-carboxylate | HCID 143452 | — |
| 반응물 | 5-Bromo-6-fluoro-2-methylquinoline | HCID 13035313 | — |
| 반응물 | Bis(diphenylphosphino)-1,1'-binaphthyl | HCID 18630801 | — |
| 용매 | Toluene | HCID 1140 | — |
| 생성물 | 1,1-Dimethylethyl 4-(6-fluoro-2-methyl-5-quinolinyl)-1-piperazinecarboxylate | HCID 57444313 | 65.8% |
반응 단계
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).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US07732600B2 |
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| 출처 데이터셋 | uspto-grants-2010_06 |
|---|
| ORD ID | ord-02bb4beb3165405caae7e9f47c14f4d6 |
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| 출처 메모 | uspto-grants-2010_06 |
|---|
