Synthesis of 5-bromopyridyl-2-magnesium chloride and its application in the synthesis of functionalized pyridines

  • Org Lett. 2004 Dec 23;6(26):4905-7. doi: 10.1021/ol0400589.
Jinhua J Song  1 ,  Nathan K Yee ,  Zhulin Tan ,  Jinghua Xu ,  Suresh R Kapadia ,  Chris H Senanayake
Affiliations
  • 1. Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Old Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. [email protected]
PMID: 15606096 DOI: 10.1021/ol0400589
Abstract

[reaction: see text] The 5-bromopyridyl-2-magnesium chloride (2), which was not accessible previously, was efficiently synthesized for the first time via an iodo-magnesium exchange reaction with 5-bromo-2-iodopyridine (1). This reactive intermediate was allowed to react with a variety of electrophiles to afford a range of useful functionalized pyridine derivatives. Application of this methodology to 5-bromo-2-iodo-3-picoline provided a simple and economical synthesis of a key intermediate for the preparation of Lonafarnib, a potent Anticancer agent.

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