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 |
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Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
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•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. |
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ISSN: | 0022-1139 1873-3328 |
DOI: | 10.1016/j.jfluchem.2020.109509 |