title: Tetrabutylammonium salt induced denitration of nitropyridines: synthesis of fluoro-, hydroxy-, and methoxypyridines.
abstract: An efficient method for the synthesis of fluoropyridines via the fluorodenitration reaction is reported. The reaction is mediated by tetrabutylammonium fluoride (TBAF) under mild conditions without undue regard to the presence of water. The fluorodenitration is general for 2- or 4-nitro-substituted pyridines, while 3-nitropyridines require attendant electron-withdrawing groups for the reaction to proceed efficiently. Nitropyridines also undergo hydroxy- and methoxydenitration under mild conditions in the presence of the corresponding tetrabutylammonium species. [reaction: see text]
authors.affiliation: Department of Medicinal Chemistry, Merck Research Laboratories, West Point, PA 19486, USA. scott_d_kuduk@merck.com
authors.forename: Scott D
authors.initials: SD
authors.lastname: Kuduk
authors.forename: Robert M
authors.initials: RM
authors.lastname: DiPardo
authors.forename: Mark G
authors.initials: MG
authors.lastname: Bock
mesh_terms: D008958:Models, Molecular; D009566:Nitrates; D009574:Nitro Compounds / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis*; D000644:Quaternary Ammonium Compounds
chemical_list: D009566:Nitrates; D009574:Nitro Compounds; D011725:Pyridines; D000644:Quaternary Ammonium Compounds; C009405:tetrabutylammonium