Cupric acetate-mediated N-arylation with aryl boronic acids proceeded regioselectively to form the N-2-substituted derivatives.
Abstract
A N-derivatized 3-dimethylaminopropyloxypyrazole library was prepared using solution-phase parallel synthesis.
The library was designed using physicochemical constraints designed to remove non-membrane-permeable molecules.
Cupric acetate-mediated N-arylation with aryl boronic acids proceeded regioselectively to form the N-2-substituted derivatives. The presence of the 3-dimethylaminopropyloxy group was found to completely control the regioselectivity of the arylation. Presence of a dimethylaminoethyloxy or dimethylaminobutyloxy group gave a lesser degree of regioselectivity. The scope of the method as applied to library synthesis is discussed.
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