Chemoselective amination of 5-bromo-2-chloro-3-fluoropyridine.
Stroup, Bryan, Szklennik, Paul, Forster, Cornelia and Serrano-Wu, Michael (2007) Chemoselective amination of 5-bromo-2-chloro-3-fluoropyridine. Organic Letters, 9 (10). pp. 2039-2042. ISSN 1523-7060
Abstract
The chemoselective functionalization of 5-bromo-2-chloro-3-fluoropyridine (1c) is described. Catalytic amination conditions (Pd2dba3, Xantphos, base) afford exclusively the bromide substitution product (2) for both secondary amines and primary anilines. A reversal in chemoselectivity is observed under neat conditions in the absence of palladium catalysis, with substitution at the 2-chloro position preferred to generate 3. Last, selective substitution of the 3-fluoro group is achieved under SNAr conditions to afford the dihalo adduct (4).
Item Type: | Article |
---|---|
Related URLs: | |
Additional Information: | archiving not formally supported by this publisher |
Related URLs: | |
Date Deposited: | 14 Dec 2009 14:00 |
Last Modified: | 31 Jan 2013 01:17 |
URI: | https://oak.novartis.com/id/eprint/436 |