Regioselective synthesis of C-2 substituted imidazo[4,5-b]pyridines utilizing palladium catalysed C–N bond forming reactions with enolizable heterocycles

In this Letter we report a rapid and facile access to C2-substituted imidazo[4,5-b]pyridine analogues utilizing palladium mediated Buchwald–Hartwig cross-coupling reactions. The use of enolizable heterocycles as cross-coupling partners resulted in a wide range of imidazo[4,5-b]pyridine analogues whi...

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Bibliographic Details
Published in:Tetrahedron letters 2014-03, Vol.55 (10), p.1778-1783
Main Authors: Abdul Khader, K.K., Sajith, Ayyiliath M., Ali Padusha, M. Syed, Nagaswarupa, H.P., Muralidharan, A.
Format: Article
Language:English
Subjects:
2-Halo imidazo[4,5-b]pyridines
Bonding
Chemical reactions
Cross coupling
C–N bond formation
Enolizable heterocycles
Joining
Nucleophiles
Palladium
Palladium mediated Buchwald–Hartwig cross-coupling reaction
Regioselective synthesis
Synthesis (chemistry)
Tetrahedrons
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Summary:In this Letter we report a rapid and facile access to C2-substituted imidazo[4,5-b]pyridine analogues utilizing palladium mediated Buchwald–Hartwig cross-coupling reactions. The use of enolizable heterocycles as cross-coupling partners resulted in a wide range of imidazo[4,5-b]pyridine analogues which are prone to have medicinal relevance. Xantphos and Pd(OAc)2 were found to be more effective for the coupling of 2-halo imidazo[4,5-b]pyridines with pyridone nucleophiles. A regioselective approach for the synthesis of 2-substituted 3H-imidazo[4,5-b]pyridine and 1H-imidazo[4,5-b]pyridine is also reported.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.01.114