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A Multifunctional Reagent Designed for the Site-Selective Amination of Pyridines

  • Patrick S. Fier*
    Patrick S. Fier
    Department of Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States
    *E-mail: [email protected]
    More by Patrick S. Fier
    Orcidhttp://orcid.org/0000-0002-6102-815X
  • , 
  • Suhong Kim
    Suhong Kim
    Department of Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States
    More by Suhong Kim
  • , and 
  • Ryan D. Cohen
    Ryan D. Cohen
    Department of Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States
    More by Ryan D. Cohen
Cite this: J. Am. Chem. Soc. 2020, 142, 19, 8614–8618
Publication Date (Web):April 23, 2020
https://doi.org/10.1021/jacs.0c03537
Copyright © 2020 American Chemical Society
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    Abstract

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    We report the development of a multifunctional reagent for the direct conversion of pyridines to Boc-protected 2-aminopyridines with exquisite site selectivity and chemoselectivity. The novel reagent was prepared on 200-g scale in a single step, reacts in the title reaction under mild conditions without precautions toward air or moisture, and is tolerant of nearly all common functionality. Experimental and in situ spectroscopic monitoring techniques provide detailed insights and unexpected findings for the unique reaction mechanism.

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