2. Academic Validation
  3. Functional Hexafluoroisopropyl Group Used in the Construction of Biologically Important Pyrimidine Derivatives

Functional Hexafluoroisopropyl Group Used in the Construction of Biologically Important Pyrimidine Derivatives

  • J Org Chem. 2024 Nov 15;89(22):16485-16492. doi: 10.1021/acs.joc.4c01749.
Shuo Yuan 1 2,  Xiang Li 3,  Yue-Lin Zhang 3,  Wen-Juan Zhou 1,  Yuan-Bing Du 4,  Zhang-Xu He 4,  Hong-Min Liu 2,  Yi-Ru Bai 1 2
Affiliations

Affiliations

  • 1 Children's Hospital Affiliated to Zhengzhou University, Henan Children's Hospital, Zhengzhou Children's Hospital, Zhengzhou 450018, China.
  • 2 School of Pharmaceutical Sciences & Key Laboratory of Advanced Drug Preparation Technologies, Zhengzhou University, Zhengzhou 450001, China.
  • 3 Department of Obstetrics and Gynecology, Zhengzhou Key Laboratory of Endometrial Disease Prevention and Treatment Zhengzhou China, The Third Affiliated Hospital of Zhengzhou University, Zhengzhou 450052, China.
  • 4 Pharmacy College, Henan University of Chinese Medicine, Zhengzhou 450046, China.
PMID: 39480993 DOI: 10.1021/acs.joc.4c01749
Abstract

A series of versatile 4-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)pyridine intermediates have been developed to efficiently produce biaryls, amines, ethers, and thioethers. These hydrolysis-stable ether intermediates exhibit reactivity toward electron-donating groups and nucleophiles in cross-coupling and nucleophilic substitution reactions while surpassing the stability of corresponding aryl halides. In comparison to conventional coupling methods, this protocol offers an alternative pathway for accessing natural product and drug-like compounds without the need for metal catalysts. With assistance of this approach, we successfully obtained a potent P-glycoprotein Inhibitor 4k (YS-370), a potent epidermal growth factor receptor inhibitor 4l (YS-363), and a promising lysine-specific demethylase 1 inhibitor 5g.

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