Synthesis of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine derivatives

Bradiaková, Ivana, Ďurčeková, Tatiana, Prónayová, Naďa, Gatial, Anton and Krutošíková, Alžbeta Synthesis of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine derivatives Chemical Papers, Vol.63, No. 5, 2009, 586-591

Document type: Článok z časopisu / Journal Article
Collection: Chemical papers  

Author(s) Bradiaková, Ivana
Ďurčeková, Tatiana
Prónayová, Naďa
Gatial, Anton
Krutošíková, Alžbeta
Title Synthesis of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine derivatives
Journal name Chemical Papers
Publication date 2009
Year available 2009
Volume number 63
Issue number 5
ISSN 0366-6352
Start page 586
End page 591
Place of publication Poland
Publisher Versita
Collection year 2009
Language english
Subject 250000 Chemical Sciences
Abstract/Summary 2-[3-(Trifluoromethyl)phenyl]-4,5-dihydrofuro[3,2-c]pyridin-4-one (I) was prepared by a three-step synthesis. Its reaction with phosphorus sulfide rendered thione II which was methylated to 2-[3-(Trifluoromethyl)phenyl]-4-methylsulfanylfuro[3,2-c]pyridine (III). 5-Methyl-2-[3-(trifluoromethyl)phenyl]-4,5-dihydrofuro[3,2-c]pyridin-4-one (IV) was obtained by the reaction of I with methyl iodide in PTC conditions. The chlorine atom in derivate V was replaced with heterocyclic secondary amines via nucleophilic substitution and 4-substituted furopyridines VIa and VIb were thus prepared. 2-[3-(Trifluoromethyl)phenyl]furo[3,2-c]pyridine-4-carboxylic acid (VII) was obtained by hydrolysis of the corresponding carbonitrile Va.
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