Method for preparing pyridine-2,3-dicarboxylic acid esters

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C546S296000, C546S299000, C546S321000

Reexamination Certificate

active

07009058

ABSTRACT:
A method for preparing pyridine-2,3-dicarboxylic acid esters of the general formula:wherein R is C1-6-alkyl, C3-6-cycloalkyl, aryl or arylalkyl, and R1to R3, independently of one another, represent hydrogen, C1-6-alkyl, fluorinated C1-6-alkyl, C1-6-alkoxy, (C1-6-alkoxy)-C1-6-alkyl or (C1-6-alkoxy)carbonyl. These esters are obtained from the corresponding 2,3-dichloropyridine, the corresponding alcohol ROH and carbon monoxide in the presence of a palladium-diphosphine complex and a weak base. Pyridine-2,3-dicarboxylic acid esters are herbicides or intermediates for the preparation of herbicides.

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Chemical Abstracts, CA Reference 132:64145, “Preparation of pyridinecarboxylates from chloropyridines by palladium-catalyzed alkoxycarbonylation” 2000, p. 682-683.
Bessard, et al., “Selective Alkoxycarbonylation of 2, 3-Dichloropyridines”, Tetrahedron 55 (1999) pp. 393-404.
CA 126:212013, “Regiospecific carboalkoxylation of 2,5-dibromopyridine,”, Chambers, p. 1, Synthetic Communications, 27 (3), 515-520.
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Paquette, L. A., Encyclopedia of Reagents for Organic Synthesis, vol. 4 (1995), pp. 2769-2771.

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