title: Synthesis of 5-bromopyridyl-2-magnesium chloride and its application in the synthesis of functionalized pyridines.
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.
authors.affiliation: Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Old Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. jsong@rdg.boehringer-ingelheim.com
authors.forename: Jinhua J
authors.initials: JJ
authors.lastname: Song
authors.forename: Nathan K
authors.initials: NK
authors.lastname: Yee
authors.forename: Zhulin
authors.initials: Z
authors.lastname: Tan
authors.forename: Jinghua
authors.initials: J
authors.lastname: Xu
authors.forename: Suresh R
authors.initials: SR
authors.lastname: Kapadia
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake
mesh_terms: D015636:Magnesium Chloride / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C510306:5-bromopyridyl-2-magnesium chloride; D009942:Organometallic Compounds; D011725:Pyridines; D015636:Magnesium Chloride