title: Copper (II)-mediated arylation with aryl boronic acids for the N-derivatization of pyrazole libraries.
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.
authors.affiliation: Biological & Medicinal Chemistry, The Wolfson Institute for Biomedical Research, University College London, Gower Street, London WC1E 6BT, UK.
authors.forename: Sharon
authors.initials: S
authors.lastname: Rossiter
authors.forename: Chi Kit
authors.initials: CK
authors.lastname: Woo
authors.forename: Basil
authors.initials: B
authors.lastname: Hartzoulakis
authors.forename: Grant
authors.initials: G
authors.lastname: Wishart
authors.forename: Lee
authors.initials: L
authors.lastname: Stanyer
authors.forename: Jeff W
authors.initials: JW
authors.lastname: Labadie
authors.forename: David L
authors.initials: DL
authors.lastname: Selwood