Tetrabutyl ammonium salt-induced denitration of nitropyridines: Synthesis of fluoro-, hydroxy-, and methoxypyridines

ORGN 152

Scott D. Kuduk, scott_d_kuduk@merck.com, Robert M. DiPardo, and Mark G. Bock. Department of Medicinal Chemistry, Merck & Co., Inc, WP14-3, Sumneytown Pike, Post Office Box 4, West Point, PA 19486
An efficient method for the synthesis of fluoropyridines via the fluorodenitration reaction is reported. The reaction is mediated by tetrabutyl ammonium fluoride (TBAF) and is carried out 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 tetrabutyl ammonium species.

 

Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005