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Regioselective palladium-catalyzed arylation of 4-chloropyrazoles. 2010

Carlos Mateos, and Javier Mendiola, and Mercedes Carpintero, and José Miguel Mínguez
Centro de Investigación Lilly S.A., Avda. de la Industria, 30, Alcobendas-Madrid 28108, Spain. c.mateos@lilly.com

A highly regioselective Pd-catalyzed arylation of N-methylpyrazoles with aryl bromides is described. This transformation was studied extensively via automated reaction screening. A Design of Experiments (DoE) approach for optimizing the critical parameters was applied, resulting in excellent conditions for preparing selectively 5-arylpyrazoles in moderate to excellent yields under mild conditions.

UI MeSH Term Description Entries
D010165 Palladium A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.
D011720 Pyrazoles Azoles of two nitrogens at the 1,2 positions, next to each other, in contrast with IMIDAZOLES in which they are at the 1,3 positions.
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D017606 Chlorine Compounds Inorganic compounds that contain chlorine as an integral part of the molecule. Chlorine Compounds, Inorganic,Compounds, Chlorine,Compounds, Inorganic Chlorine,Inorganic Chlorine Compounds

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