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Synthesis 2012(5): 735-746  
DOI: 10.1055/s-0031-1289687
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Noncryogenic Synthesis of Functionalized 2-Methoxypyridines by Halogen-Magnesium Exchange Using Lithium Dibutyl(isopropyl)magnesate(1-) and Lithium Chloride

Łukasz Struk, Jacek G. Sośnicki*
West Pomeranian University of Technology, Szczecin, Institute of Chemistry and Environmental Protection, Al. Piastów 42, 71065 Szczecin, Poland
Fax: +48(91)4494639; e-Mail: sosnicki@zut.edu.pl; e-Mail: lukasz.struk@zut.edu.pl ;
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Publication History

Received 26 November 2011
Publication Date:
06 February 2012 (online)

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Abstract

2-Methoxypyridines functionalized in the 3-, 5-, or 6-position and 2,6-dimethoxypyridines functionalized in the 3-position were prepared from the corresponding bromo or iodo analogues by using lithium dibutyl(isopropyl)magnesate(1-) and lithium chloride under noncryogenic conditions. The procedure was optimized in terms of the choice between two magnesates and the presence or absence of lithium chloride in the reaction medium.

Key words

pyridines - magnesium - lithium - organometallic reagents

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10

Examples of functionalization of 2-methoxypyridines by using butyllithium at low temperatures can be found in ref. 4c, 7e.