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Published on: November 30, 2022
Copper (II)-mediated arylation with aryl boronic acids for the N-derivatization of pyrazole libraries
Sharon Rossiter1, Chi Kit Woo, Basil Hartzoulakis
1Biological & Medicinal Chemistry, The Wolfson Institute for Biomedical Research, University College London, Gower Street, London WC1E 6BT, UK.
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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