A convenient approach to 3-trifluoromethyl-6-azaindoles

[Display omitted] •2-Trifluoromethyl-6-azaindole and its derivatives.•Hydration of 2,2,2-Trifluoro-1-(2-(trifluoromethyl)-1H-pyrrolo[2,3-c]pyridine-3-yl)ethanone.•Partially reduced 2-trifluoromethyl-6-azaindole derivatives. A new method for the synthesis of 2-trifluoromethyl-6-azaindole 4is proposed...

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Veröffentlicht in:Journal of fluorine chemistry 2020-05, Vol.233, p.109509, Article 109509
Hauptverfasser: Ivonin, Sergey P., Yurchenko, Aleksandr A., Voloshchuk, Volodymyr V., Yurchenko, Sergey A., Rusanov, Eduard B., Pirozhenko, Vladimir V., Volochnyuk, Dmitriy M., Kostyuk, Aleksandr N.
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Sprache:eng
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Zusammenfassung:[Display omitted] •2-Trifluoromethyl-6-azaindole and its derivatives.•Hydration of 2,2,2-Trifluoro-1-(2-(trifluoromethyl)-1H-pyrrolo[2,3-c]pyridine-3-yl)ethanone.•Partially reduced 2-trifluoromethyl-6-azaindole derivatives. A new method for the synthesis of 2-trifluoromethyl-6-azaindole 4is proposed. The method is a catalyst free, simple and scalable starting from available 3-amino-4-methylpyridine. Hydration of the trifluoracetyl derivative 2 in hydrochloric acid afforded its ketal salt 3. The molecular structures of both compounds were determined by single-crystal X-ray diffraction. The efficient scalable synthetic route to 2-trifluoromethyl 6-azaindole made possible synthesis of a variety of 3-substituted 2-trifluoromethyl 6-azaindoles and their partially saturated derivatives.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2020.109509