A convenient route to functionalized 3-amino- N-methylfuro[3,2- b]pyridine-2-carboxamides

The synthesis of novel functionalized 3-amino- N-methylfuro[3,2- b]pyridine-2-carboxamides is described from cyanopyridine intermediates. Based on the difference in halogen reactivity, ethyl [(5-bromo-2-chloropyridin-3-yl)oxy]acetate was functionalized by a palladium-catalyzed reaction, before the c...

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Bibliographic Details
Published in:Tetrahedron 2011-07, Vol.67 (26), p.4767-4773
Main Authors: Bretéché, Anne, Marchand, Pascal, Nourrisson, Marie-Renée, Hautefaye, Patrick, De Nanteuil, Guillaume, Duflos, Muriel
Format: Article
Language:English
Subjects:
3-Amino- N-methylfuro[3,2- b]pyridine-2-carboxamides
[6-Chloro-5-(2-ethoxy-2-oxoethoxy)pyridin-3-yl]benzoic acid
Chemical reactivity
Chemistry
Ethyl 3-aminomethylfuro[3,2- b]pyridine-2-carboxylates
Exact sciences and technology
Functionalized furo[3,2- b]pyridines
Halogens
Heteroannulation
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Reactivity and mechanisms
Synthesis (chemistry)
Tetrahedrons
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Description
Summary:The synthesis of novel functionalized 3-amino- N-methylfuro[3,2- b]pyridine-2-carboxamides is described from cyanopyridine intermediates. Based on the difference in halogen reactivity, ethyl [(5-bromo-2-chloropyridin-3-yl)oxy]acetate was functionalized by a palladium-catalyzed reaction, before the cyclization to the desired furo[3,2- b]pyridines. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.05.035