The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Oct. 02, 2018

Filed:

May. 19, 2017
Applicant:

Dow Agrosciences Llc, Indianapolis, IN (US);

Inventors:

Jason S. Fisk, Freeland, MI (US);

Xiaoyong Li, Midland, MI (US);

Mark Muehlfeld, Midland, MI (US);

Robert S. Bauman, Bay City, MI (US);

Jossian Oppenheimer, Midland, MI (US);

Siyu Tu, Midland, MI (US);

Mark A. Nitz, Midland, MI (US);

Reetam Chakrabarti, Collegeville, PA (US);

Shawn D. Feist, Midland, MI (US);

James W. Ringer, Midland, MI (US);

Ronald B. Leng, Midland, MI (US);

Assignee:

Dow AgroSciences LLC, Indianapolis, IN (US);

Attorney:
Primary Examiner:
Int. Cl.
CPC ...
C07D 213/90 (2006.01); C07D 401/04 (2006.01); C07D 239/28 (2006.01); B01J 35/00 (2006.01); C07D 213/79 (2006.01); C07D 239/02 (2006.01); C07D 239/32 (2006.01);
U.S. Cl.
CPC ...
C07D 401/04 (2013.01); B01J 35/0046 (2013.01); C07D 213/79 (2013.01); C07D 213/90 (2013.01); C07D 239/02 (2013.01); C07D 239/28 (2013.01); C07D 239/32 (2013.01); B01J 2231/4211 (2013.01);
Abstract

Improved methods of synthesizing 6-aryl-4-aminopicolinates, such as arylalkyl and alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates and arylalkyl and alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates, are described herein. The improved methods include a direct Suzuki coupling step, which eliminates the protection/de-protection steps in the current chemical process, and therefore eliminates or reduces various raw materials, equipment and cycle time as well as modification of other process conditions including use of crude AP, use of ABA-diMe, and varying pH, catalyst concentration, solvent composition, and/or workup procedures. This invention was expanded to include synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates.


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