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

✍ Scribed by Ivana Bradiaková; Tatiana Ďurčeková; Naďa Prónayová; Anton Gatial; Alžbeta Krutošíková

• Book ID: 111491270
• Publisher: Versita
• Year: 2009
• Tongue: English
• Weight: 365 KB
• Volume: 63
• Category: Article
• ISSN: 0366-6352
• DOI: 10.2478/s11696-009-0052-4

✦ Synopsis

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.