Copper-Mediated Aminoquinoline-Directed Radiofluorination of Aromatic C−H Bonds with K18F
Dr. So Jeong Lee
Department of Radiology, University of Michigan, 1301 Catherine St, Ann Arbor, MI, 48109 USA
Search for more papers by this authorKatarina J. Makaravage
Department of Chemistry, The University of Michigan, 930 North University Ave, Ann Arbor, MI, 48109 USA
Search for more papers by this authorDr. Allen F. Brooks
Department of Radiology, University of Michigan, 1301 Catherine St, Ann Arbor, MI, 48109 USA
Search for more papers by this authorCorresponding Author
Prof. Peter J. H. Scott
Department of Radiology, University of Michigan, 1301 Catherine St, Ann Arbor, MI, 48109 USA
Search for more papers by this authorCorresponding Author
Prof. Melanie S. Sanford
Department of Chemistry, The University of Michigan, 930 North University Ave, Ann Arbor, MI, 48109 USA
Search for more papers by this authorDr. So Jeong Lee
Department of Radiology, University of Michigan, 1301 Catherine St, Ann Arbor, MI, 48109 USA
Search for more papers by this authorKatarina J. Makaravage
Department of Chemistry, The University of Michigan, 930 North University Ave, Ann Arbor, MI, 48109 USA
Search for more papers by this authorDr. Allen F. Brooks
Department of Radiology, University of Michigan, 1301 Catherine St, Ann Arbor, MI, 48109 USA
Search for more papers by this authorCorresponding Author
Prof. Peter J. H. Scott
Department of Radiology, University of Michigan, 1301 Catherine St, Ann Arbor, MI, 48109 USA
Search for more papers by this authorCorresponding Author
Prof. Melanie S. Sanford
Department of Chemistry, The University of Michigan, 930 North University Ave, Ann Arbor, MI, 48109 USA
Search for more papers by this authorGraphical Abstract
Late-stage fluorination: K18F is applied in a newly developed Cu-mediated ortho-C(sp2)−H radiofluorination of aromatic carboxylic acids that are protected as 8-aminoquinoline benzamides. Fluorination of 18 examples in up to 62 % radiochemical yield and high specific activity is reported, including the automated synthesis of [18F]AC261066.
Abstract
A Cu-mediated ortho-C−H radiofluorination of aromatic carboxylic acids that are protected as 8-aminoquinoline benzamides is described. The method uses K18F and is compatible with a wide range of functional groups. The reaction is showcased in the high specific activity automated synthesis of the RARβ2 agonist [18F]AC261066.
Supporting Information
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