title: An efficient, regioselective amination of 3,5-disubstituted pyridine N-oxides using saccharin as an ammonium surrogate.
abstract: A process for the regioselective amination of unsymmetrical 3,5-substituted pyridine N-oxides has been developed utilizing cheap, readily available saccharin as an ammonium surrogate. High conversions of the corresponding saccharin adducts have been achieved under mild reaction conditions. In situ deprotection under acidic conditions allows for a one-pot process to substituted aminopyridines. High regioselectivities were obtained from a variety of 3,5-disubstituted pyridine N-oxides.
authors.affiliation: Chemical Process Research and Development, Amgen Inc., One Amgen Center Drive, Thousand Oaks, California 91320, USA. rfarrell@amgen.com
authors.forename: Robert P
authors.initials: RP
authors.lastname: Farrell
authors.forename: Maria Victoria
authors.initials: MV
authors.lastname: Silva Elipe
authors.forename: Michael D
authors.initials: MD
authors.lastname: Bartberger
authors.forename: Jason S
authors.initials: JS
authors.lastname: Tedrow
authors.forename: Filisaty
authors.initials: F
authors.lastname: Vounatsos
mesh_terms: D000586:Amination; D000631:Aminopyridines / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012439:Saccharin / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000631:Aminopyridines; D011725:Pyridines; D000644:Quaternary Ammonium Compounds; C013229:pyridine N-oxide; D012439:Saccharin