H. Xiong, Adam T. Hoye, Kuo‐hsien Fan
Jul 20, 2015
Citations
1
Influential Citations
42
Citations
Journal
Organic letters
Abstract
Among known precursors for 2-[(18)F]fluoropyridines, pyridyltrialkylammonium salts have shown excellent reactivity; however, their broader utility has been limited because synthetic methods for their preparation suffer from poor functional group compatibility. In this paper, we demonstrate the regioselective conversion of readily available pyridine N-oxides into 2-pyridyltrialkylammonium salts under mild and metal-free conditions. These isolable intermediates serve as effective precursors to structurally diverse 2-fluoropyridines, including molecules relevant to PET imaging. In addition to providing access to nonradioactive analogues, this method has been successfully applied to (18)F-labeling in the radiosynthesis of [(18)F]AV-1451 ([(18)F]T807), a PET tracer currently under development for imaging tau.