Electrophilic fluorination: the aminopyridine dilemma

Author:

Fields Stephen C.,Lo William C.,Brewster William K.,Lowe Christian T.

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference33 articles.

1. Common name 4-amino-3,6-dichloropicolinic acid, sold under the tradename Milestone™ (among others): Alexander, A. L.; Balko, T. W.; Bjelk, L. A.; Buysse, A. M.; Fields, S. C.; Keese, R.; Krumel, K. L.; Lo, W. C.; Lowe, C. T.; Richburg, J. S.; Ruiz, J. M. 4-Aminopicolinates and Their Use as Herbicides. U.S. Patent 6,297,197, Oct. 2, 2001; Chem. Abstr. 2001, 135, 107254.

2. Johnston, H.; Tomita, M. S. Amino-trichloropicolinic acid compounds. U.S. Patent 3,285,925, Nov. 15, 1966; Chem. Abstr. 1967, 66, 46338.

3. Balko, T. W.; Buysse, A. M.; Epp, J. B.; Fields, S. C.; Lowe, C. T.; Keese, R. J.; Richburg, J. S., III; Ruiz, J. M.; Weimer, M. R.; Green, R. A.; Gast, R. E.; Bryan, K.; Irvine, N. M.; Lo, W. C.-L.; Brewster, W. K.; Webster, J. D. 6-Aryl-4-aminopicolinates and Their Use as Herbicides. U. S. Patent 6,784,137, Aug. 31, 2004; Chem. Abstr. 2003, 138, 153444.

4. Aminopyralid (3) is currently synthesized by the electrochemical reduction of picloram (4) at Dow on production scale.

5. Krumel, K. L.; Bott, C. J.; Gullo, M. F.; Hull, J. W., Jr.; Scortichini, C. L. Selective electrochemical reduction of halogenated 4-aminopicolinic acids. U. S. Patent 6,352,635, Mar. 5, 2002; Chem. Abstr. 2001, 135, 98860.

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