Preparation of N-alkylated pyridones via selective N-alkylation of 2-alkoxypyridines on solid phase

Marcus C Ruda; Jan Bergman; Jinchang Wu

doi:10.1021/cc020036i

Preparation of N-alkylated pyridones via selective N-alkylation of 2-alkoxypyridines on solid phase

J Comb Chem. 2002 Sep-Oct;4(5):530-5. doi: 10.1021/cc020036i.

Authors

Marcus C Ruda¹, Jan Bergman, Jinchang Wu

Affiliation

¹ Karo Bio AB, Novum, SE-14157 Huddinge, Sweden. marcus.ruda@karobio.se

PMID: 12217027
DOI: 10.1021/cc020036i

Abstract

Regioselective solid-phase synthesis of N-alkylated 2-pyridones has been carried out starting from 2-halopyridines. Variously substituted 2-halopyridines were linked to a Wang resin in quantitative yields to afford 2-alkoxypyridines. The coupled products were then reacted with a variety of alkyl halides, resulting in tandem alkylation and cleavage from the resin to generate N-alkylated pyridones with no detectable traces of O-alkylated products. The scope and limitations of this exceptionally selective reaction have been studied.