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Method for Preparing 2-Aminobenzamide Derivatives

IP.com Disclosure Number: IPCOM000238686D
Publication Date: 2014-Sep-11
Document File: 2 page(s) / 86K

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The IP.com Prior Art Database

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               Title
Method for Preparing 2-Aminobenzamide Derivatives

Abstract

   Disclosed is a method for the preparation of 2-aminobenzamides by carboamidation of 2- aminoaryl halides utilizing a palladium-based catalyst system containing a sub-stoichiometric amount of a phenoxide salt additive.

Disclosure

   Preparation of certain 2-aminobenzamides and their utility as intermediates for preparing insecticidal anthranilic diamides is disclosed in PCT Patent Publication WO2006/062978.

   The currently disclosed method for preparing compounds of Formula 1 comprises contacting a compound of Formula 2 with a compound of Formula 3 in the presence of carbon monoxide, a palladium source, a ligand, and a base of Formula 4

wherein

R1 is F, Cl, C1-C4 alkyl, C1-C4 fluoroalkyl, C1-C4 alkoxy or C1-C6 haloalkoxy; R2 is F, Cl or cyano;

R3 is H, C1-C4 alkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, or C4-C7 alkylcycloalkyl;

X is Br or I;

Ar is phenyl optionally substituted with halogen, C1-C4 alkyl or C1-C4 fluoroalkyl;

and


M is lithium, sodium, potassium or cesium.

   The palladium source used in this method may be either palladium(0) or palladium(II) compounds. The ligand may be a monodentate or bidentate phosphine, but bidentate phosphines are preferred. Compatible solvents may be used as a medium for the reaction. Suitable solvents include ethers, nitriles, aromatic hydrocarbons and alcohols, and mixtures thereof. The preferred palladium sources, ligands, and solvents are shown in Table 1. The pre...