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Synthesis 2009(1): 155-159  
DOI: 10.1055/s-0028-1083268
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Thermal Amination of 2,6-Dihalopyridines by Sterically Demanding Amines

Andreas Fausta, Oliver Wolffb, Siegfried R. Waldvogel*b
a Klinik und Poliklinik für Nuklearmedizin, Universitätsklinikum Münster, Domagkstr. 5, 48149 Münster, Germany
b Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
Fax: +49(228)739608; e-Mail: waldvogel@uni-bonn.de;
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Publication History

Received 9 November 2008
Publication Date:
12 December 2008 (online)

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Abstract

When transition-metal-catalyzed transformations fail, the amination reaction of activated bromo- and chloropyridines can be achieved thermally. The auxiliary base 2,2,6,6-tetramethylpiperidine turned out to be the key for the conversion of highly sterically demanding and acid labile amines.

Key words

aminations - nucleophilic aromatic substitutions - steric hindrance - pyridines - tetramethylpiperidine

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15

Compounds 4 and 5 were identified by GC/MS and ¹H NMR spectroscopy.