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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
Author(s) -
Rosenberg Adam J.,
Ahmed Ijaz,
Wilson Robert J.,
Williams Theresa M.,
Kaminsky Lauren,
Clark Daniel A.
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400465
Subject(s) - chemistry , xantphos , palladium , phosphine , catalysis , ligand (biochemistry) , medicinal chemistry , combinatorial chemistry , solvent , organic chemistry , stereochemistry , receptor , biochemistry
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.