Sulfone-Mediated SNAr Reaction as a Powerful Tool for the Synthesis of 4-Quinolinyl Ethers and More-Application to the Synthesis of HCV NS3/4a Protease Inhibitor BI 201420.,The Journal of Organic Chemistry

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Sulfone-Mediated SNAr Reaction as a Powerful Tool for the Synthesis of 4-Quinolinyl Ethers and More-Application to the Synthesis of HCV NS3/4a Protease Inhibitor BI 201420.
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2020-05-28 , DOI: 10.1021/acs.joc.0c00554
Nitinchandra D Patel ₁ , Xudong Wei ₁ , Denis Byrne ₁ , Bikshandarkoil A Narayanan ₁ , Scott Pennino ₂ , Max Sarvestani ₁ , Anjan Saha ₁ , Nizar Haddad ₁ , Suresh Kapadia ₁ , Jon C Lorenz ₁ , Philomen DeCroos ₁ , Andrew Ye ₁ , Heewon Lee ₁ , Nelu Grinberg ₁ , Azad Hossain ₁ , Carl A Busacca ₁ , Nathan K Yee ₁ , Chris H Senanayake ₁

Affiliation

An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive S_NAr reaction of 4-quinolinyl sulfones with a range of structurally diversified 1°, 2°, and 3° alcohols with a wide substrate scope and high yields. By adapting this methodology, a convergent synthesis of a complex target of HCV NS3/4a protease inhibitor BI 201420 was accomplished.

中文翻译：

砜介导的SNAr反应可作为合成4-喹啉基醚的有力工具，并在HCV NS3 / 4a蛋白酶抑制剂BI 201420的合成中具有更多应用。

通过4-喹啉基砜与一系列结构多样的1°，2°和3°醇的高反应性S _N Ar反应，证明了合成4-喹啉基醚的有效通用方法，该方法具有广泛的底物范围和较高的产量。通过采用这种方法，可以完成HCV NS3 / 4a蛋白酶抑制剂BI 201420复杂靶标的融合合成。

更新日期：2020-07-02

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