An Improved Synthesis of Imidazo[4,5-b]pyridines and Imidazo[4,5-b]pyrazines by Palladium Catalyzed Amidation using Xantphos in a 1,4-Dioxane:tert-Amyl Alcohol Solvent System

Herein an improved protocol for the synthesis of imidazo[4,5‐b]pyridines and imidazo[4,5‐b]pyrazines using a palladium‐catalyzed amidation that utilizes Xantphos as an ancillary phosphine ligand is reported. The use of a binary solvent system comprised of 1,4‐dioxane and tert‐amyl alcohol was crucia...

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Veröffentlicht in:Advanced synthesis & catalysis 2014-11, Vol.356 (16), p.3465-3470
Hauptverfasser: Rosenberg, Adam J., Ahmed, Ijaz, Wilson, Robert J., Williams, Theresa M., Kaminsky, Lauren, Clark, Daniel A.
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container_end_page 3470
container_issue 16
container_start_page 3465
container_title Advanced synthesis & catalysis
container_volume 356
creator Rosenberg, Adam J.
Ahmed, Ijaz
Wilson, Robert J.
Williams, Theresa M.
Kaminsky, Lauren
Clark, Daniel A.
description Herein an improved protocol for the synthesis of imidazo[4,5‐b]pyridines and imidazo[4,5‐b]pyrazines using a palladium‐catalyzed amidation that utilizes Xantphos as an ancillary phosphine ligand is reported. The use of a binary solvent system comprised of 1,4‐dioxane and tert‐amyl alcohol was crucial in eliminating unwanted by‐products.
doi_str_mv 10.1002/adsc.201400465
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source Wiley Journals
subjects Alcohols
Byproducts
Catalysis
Ligands
nitrogen heterocycles
P ligands
Palladium
Phosphines
Solvents
Synthesis
title An Improved Synthesis of Imidazo[4,5-b]pyridines and Imidazo[4,5-b]pyrazines by Palladium Catalyzed Amidation using Xantphos in a 1,4-Dioxane:tert-Amyl Alcohol Solvent System
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