참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Cesium carbonate | HCID 10796 | — |
| 반응물 | 2-Cyanophenylboronic acid | HCID 2734610 | — |
| 반응물 | Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate | HCID 10991161 | — |
| 용매 | Water | HCID 962 | — |
| 용매 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 생성물 | tert-butyl 4-(2-cyanophenyl)-5,6-dihydropyridine-1(2H)-carboxylate | HCID 18326592 | 51.6% |
반응 단계
4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.5 g, 1.5 mmol), 2-cyanophenylboronic acid (0.23 g, 1.6 mmol), tetrakis-triphenylphosphine (0.17 g, 0.15 mmol) and cesium carbonate (0.73 g, 2.26 mmol) were dissolved in a mixture of DME (3 mL), IMS (1.0 mL) and water (0.4 mL) under argon. The mixture was heated by microwave irradiation to 120° C. for 0.3 hours then diluted with water. The products were extracted into DCM, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 0-20% ethyl acetate/hexane. The fractions containing the desired product were concentrated under vacuum to give the title compound as a yellow oil (0.22 g). LCMS m/z 261.2 [M+H]+. R.T.=4.59 min (Analytical Method 4).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US08642621B2 |
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| 출처 데이터셋 | uspto-grants-2014_02 |
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| ORD ID | ord-1a6eb3fef2f14ed88af10f8a85558141 |
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| 출처 메모 | uspto-grants-2014_02 |
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