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        Copper (II) mediated arylation with aryl boronic acids for the N-derivatization of pyrazole libraries

        Author
        Rossiter, S.
        Woo, C.K.
        Hartzoulakis, B.
        Wishart, G.
        Stanyer, L.
        Labadie, J.W.
        Selwood, D.L.
        Attention
        2299/2621
        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.
        Publication date
        2004
        Published in
        Journal of Combinatorial Chemistry
        Published version
        https://doi.org/10.1021/cc034065k
        Other links
        http://hdl.handle.net/2299/2621
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