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Synthesis 2012(5): 735-746
DOI: 10.1055/s-0031-1289687
DOI: 10.1055/s-0031-1289687
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkNoncryogenic Synthesis of Functionalized 2-Methoxypyridines by Halogen-Magnesium Exchange Using Lithium Dibutyl(isopropyl)magnesate(1-) and Lithium Chloride
Further Information
Received
26 November 2011
Publication Date:
06 February 2012 (online)
Publication History
Publication Date:
06 February 2012 (online)

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