Facile Route to 2-Fluoropyridines via 2-Pyridyltrialkylammonium Salts Prepared from Pyridine N-Oxides and Application to (18)F-Labeling.
Org Lett
; 17(15): 3726-9, 2015 Aug 07.
Article
en En
| MEDLINE
| ID: mdl-26193373
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.
Texto completo:
1
Bases de datos:
MEDLINE
Asunto principal:
Piridinas
/
Compuestos de Amonio Cuaternario
/
Hidrocarburos Fluorados
Idioma:
En
Revista:
Org Lett
Asunto de la revista:
BIOQUIMICA
Año:
2015
Tipo del documento:
Article
País de afiliación:
Estados Unidos