Directed solid-phase synthesis of trisubstituted imidazo[4,5-c]pyridines and imidazo[4,5-b]pyridines

ACS Comb Sci. 2014 Oct 13;16(10):558-65. doi: 10.1021/co500090t. Epub 2014 Jul 31.


An efficient method is described for the solid-supported synthesis of imidazo[4,5-b]pyridines and imidazo[4,5-c]pyridines from 2,4-dichloro-3-nitropyridine. The key pyridine building block was reacted with polymer-supported amines, followed by replacement of the second chlorine with amines, nitro group reduction, and imidazole ring closure with aldehydes. Depending on the combination of polymer-supported and solution-phase reagents, the strategy allowed for the simple preparation of the target trisubstituted derivatives with variable positioning of the pyridine nitrogen atom. Additionally, after a slight modification of the method, the preparation of strictly isomeric imidazopyridines was possible.

Keywords: 1-deazapurines; 2,4-dichloronitropyridine; 3-deazapurines; imidazo[4,5-b]pyridines; imidazo[4,5-c]pyridines; solid-phase synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Imidazoles / chemical synthesis*
  • Indicators and Reagents
  • Isomerism
  • Pyridines / chemical synthesis*
  • Solid-Phase Synthesis Techniques*
  • Structure-Activity Relationship


  • Aldehydes
  • Imidazoles
  • Indicators and Reagents
  • Pyridines