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