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

Adam J. Rosenberg; Ijaz Ahmed; Robert J. Wilson; Theresa M. Williams; Lauren Kaminsky; Daniel A. Clark

doi:10.1002/adsc.201400465

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

Adam J. Rosenberg, Ijaz Ahmed, Robert J. Wilson, Theresa M. Williams, Lauren Kaminsky, Daniel A. Clark

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	3465-3470
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	356
Issue number	16
DOIs	https://doi.org/10.1002/adsc.201400465
State	Published - Nov 3 2014

Keywords

Nitrogen heterocycles
P ligands
Palladium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201400465

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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. / Rosenberg, Adam J.; Ahmed, Ijaz; Wilson, Robert J. et al.
In: Advanced Synthesis and Catalysis, Vol. 356, No. 16, 03.11.2014, p. 3465-3470.

Research output: Contribution to journal › Article › peer-review

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abstract = "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.",

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AU - Rosenberg, Adam J.

AU - Ahmed, Ijaz

AU - Wilson, Robert J.

AU - Williams, Theresa M.

AU - Kaminsky, Lauren

AU - Clark, Daniel A.

PY - 2014/11/3

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N2 - 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.

AB - 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.

KW - Nitrogen heterocycles

KW - P ligands

KW - Palladium

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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