Affiliation:
1. Institute of Organic Chemistry of the National Academy of Sciences of Ukraine
2. Institute of Organic Chemistry of the National Academy of Sciences of Ukraine; Enamine Ltd.
Abstract
A practical and convenient method for synthesizing nicotinic acid and nicotinamide with the trifluoromethoxy group in position 5 of the ring has been developed. A series of related compounds, for example, nicotinic aldehyde and nicotinic alcohol, have been synthesized. It has been shown that 3-bromo-5-trifluoromethoxypyridine is a convenient and efficient synthon for palladium-catalyzed coupling reactions. The trifluoromethoxy group has been found to be remarkably stable against hydroiodic acid in contrast to the methoxy group.
Publisher
National University of Pharmacy
Reference13 articles.
1. Inoue, M.; Sumii, Y.; Shibata, N. Contribution of Organofluorine Compounds to Pharmaceuticals. ACS Omega 2020, 5 (19), 10633–10640. https://doi.org/10.1021/acsomega.0c00830.
2. Five-membered heterocyclic compound with fluoroalkoxy substituents;Davydova;Ukrainian Chemistry Journal,2015
3. Kolomeitsev, A. ; Vorobyev, M.; Gillandt, H. Versatile application of trifluoromethyl triflate. Tetrahedron Lett. 2008, 8 (3), 449-454. https://doi.org/10.1016/j.tetlet.2007.11.105.
4. Synthesis of derivatives of phenyl trifluoromethyl ethers;Yagupolskii;Dokl. Acad. Nauk SSSR,1955
5. Fuss, A.; Koch, V. Chemistry of 3-Hydroxypyridine Part 3: Synthesis of Substituted 3-[Fluoro(chloro)alkoxy]pyridines from Halo- or Amino-3-hydroxypyridines. Synthesis 1990, 7, 604-608. https://doi.org/10.1055/s-1990-26956.