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

  • Ivana Bradiaková EMAIL logo , Tatiana Ďurčeková , Naďa Prónayová , Anton Gatial and Alžbeta Krutošíková
Published/Copyright: August 25, 2009
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Abstract

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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Published Online: 2009-8-25
Published in Print: 2009-10-1

© 2009 Institute of Chemistry, Slovak Academy of Sciences

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