Regioselective palladium catalyzed synthesis of benzimidazoles and azabenzimidazoles

US8188282B2 · kind B2 · utility

Assignee

• Sanofi-Aventis · FR

Inventors

• Jorge Alonso · Mannheim, DE
• Andreas Lindenschmidt · Bad Soden, DE
• Marc Nazare · Idstein, DE
• Nis Halland · Frankfurt am Main, DE
• Omar Rkyek · Tangier, MA
• Matthias Urmann · Eschborn, DE

Key dates

• Filing date: Jan 14, 2009
• Grant date: May 29, 2012
• Expiry date: Aug 23, 2030

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D471/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention relates to a process for the regioselective synthesis of compounds of the formula I,wherein R0; R1; R2; R3; R4; R5; A1; A2; A3; A4, Q and J have the meanings indicated in the claims. The present invention provides a direct palladium catalyzed, regioselective process to a wide variety of unsymmetrical, multifunctional N-substituted benzimidazoles or azabenzimidazoles of formula I starting from 2-halo-nitroarenes and N-substituted amides useful for the production of pharmaceuticals, diagnostic agents, liquid crystals, polymers, herbicides, fungicidals, nematicidals, parasiticides, insecticides, acaricides and arthropodicides.