Synthesis of aminopyridines from 2-fluoropyridine and lithium amides

ORGN 614

Bakthan Singaram, singaram@chemistry.ucsc.edu1, Lubov Pasumansky1, Soya Gamsey1, Armando R. Hernandez1, and Christian T. Goralski2. (1) Department of Chemistry and Biochemistry, University of California, Santa Cruz, 1156 High St., Santa Cruz, CA 95064, (2) Dowpharma, Dow Chemical Company, Midland, MI 48674
Lithium amides promote the amination of 2-fluoropyridine under mild reaction conditions, providing 2-aminopyridines in good yields and purity.  Treatment of 2-fluoropyridine with 1 equiv of lithium amide at room temperature affords complete conversion after 2 h.  To our knowledge, this is the first study of lithium amide-promoted amination of fluoropyridines that are not further activated by electron-withdrawing groups

 

New Reactions and Methodology
8:00 AM-12:00 PM, Wednesday, 16 March 2005 Convention Center -- Ballroom 20 C-D, Oral

Division of Organic Chemistry

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