Copper (II)-Mediated Arylation with Aryl Boronic Acids for the N-Derivatization of Pyrazole Libraries

Autor: Rossiter, S., Woo, C. K., Hartzoulakis, B., Wishart, G., Stanyer, L., Labadie, J. W., Selwood, D. L.
Zdroj: Journal of Combinatorial Chemistry; May 2004, Vol. 6 Issue: 3 p385-390, 6p
Abstrakt: 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.
Databáze: Supplemental Index