Palladium-Catalyzed Suzuki Cross-Coupling of 2-Halo-Deazapurines with Potassium Organotrifluoroborate Salts in the Regioselective Synthesis of Imidazo[4,5-b]pyridine Analogues
In this paper, we report the use of potassium organotrifluoroborate salts as nucleophilic organoboron reagents in the Suzuki cross-coupling reactions of 2-halo deazapurines. Regio-isomeric C-2-substituted imidazo[4,5-b]pyridine analogues were synthesized by employing this protocol in good to excellent yields. Whereas aryl and heteroaryl trifluoroborates reacted readily to give the coupled products in high yields, alkyltrifluoroborates were found to be less reactive. The utilization of tetrabutylammonium acetate was found to play a substantial role in enhancing the reaction rates of the cross-coupling process. Also, a comparative study was performed between boronic acids and potassium organotrifluoroborate salts.
Savitha, Bhaskaran,Sajith, Ayyiliath. M.,Joy, M. Nibin,Khader, K.K. Abdul,Muralidharan,Padusha, M. Syed Ali,Bodke, Yadav D.
p. 618 - 630
(2016/07/06)
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
Rosenberg, Adam J.,Ahmed, Ijaz,Wilson, Robert J.,Williams, Theresa M.,Kaminsky, Lauren,Clark, Daniel A.
p. 3465 - 3470
(2015/01/09)
Synthesis of imidazo[4,5-b]pyridines and imidazo[4,5-b]pyrazines by palladium catalyzed amidation of 2-chloro-3-amino-heterocycles
A facile synthesis of imidazo[4,5-b]pyridines and-pyrazines is described using a Pd-catalyzed amide coupling reaction. This reaction provides quick access to products with substitution at N1 and C2. A model system relevant to the natural product pentosidi
Rosenberg, Adam J.,Zhao, Jinbo,Clark, Daniel A.
p. 1764 - 1767
(2012/05/20)
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