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Electrophilic fluorination: the aminopyridine dilemma
Authors:Stephen C Fields  William K Brewster  Christian T Lowe
Institution:a Discovery Research, Dow AgroSciences, Dow Venture Center, 9330 Zionsville Road, Indianapolis, IN 46268-1053, USA
b Lexington Pharmaceuticals, West Lafayette, IN 47906, USA
Abstract:An unusually high yielding fluorination of aminopyralid (3) using F-TEDA (SELECTFLUOR™) in warm water, followed by kinetic resolution (via iterative esterification/saponification) of the crude fluorination product with dry HCl in methanol produced pure ring-fluorinated pyridine 2 in an overall yield of 31% for the two steps.
Keywords:Electrophilic fluorination  Aminopyridine  F-TEDA
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