Alkylation of 3-substituted pyrazoles usually occurs at the N1 nitrogen. A highly efficient and regioselective Mg-catalyzed alkylation of these compounds has been developed to provide instead the N2 substituted regioisomers. Using 2-bromo acetates and acetamides as alkylating agents this new method was applied to a variety of 3-substituted and 3, 4-disubstituted pyrazoles to produce the N2-alkylated products with high regioselectivity and yield. The substrate scope and general applicability of this methodology will be discussed in detail.

Magnesium-catalyzed regioselective alkylation of 3-substituted pyrazoles

2019 Fall National Meeting

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