Regioselective synthesis of benzimidazole thiophene inhibitors of polo-like kinase 1

Keith R. Hornberger; Jennifer G. Badiang; James M. Salovich; Kevin W. Kuntz; Kyle A. Emmitte; Mui Cheung

doi:10.1016/j.tetlet.2008.08.077

Regioselective synthesis of benzimidazole thiophene inhibitors of polo-like kinase 1

Keith R. Hornberger, Jennifer G. Badiang, James M. Salovich, Kevin W. Kuntz, Kyle A. Emmitte, Mui Cheung

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

25 Scopus citations

Abstract

A regioselective synthesis of novel 1-(2-thienyl)-benzimidazole inhibitors of polo-like kinase 1 is described. Amination of substituted 2-iodo or -bromo nitrobenzenes with a 2-aminothiophene derivative catalyzed by Pd₂dba₃ and XANTPHOS in the presence of excess Cs₂CO₃ afforded good yields of the coupled products. Subsequent reduction and cyclization of these intermediates provided the desired benzimidazole compounds.

Original language	English
Pages (from-to)	6348-6351
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2008.08.077
State	Published - 27 Oct 2008

Keywords

Amination
Benzimidazoles
Catalysis
PLK
Palladium-catalyzed

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10.1016/j.tetlet.2008.08.077

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title = "Regioselective synthesis of benzimidazole thiophene inhibitors of polo-like kinase 1",

abstract = "A regioselective synthesis of novel 1-(2-thienyl)-benzimidazole inhibitors of polo-like kinase 1 is described. Amination of substituted 2-iodo or -bromo nitrobenzenes with a 2-aminothiophene derivative catalyzed by Pd2dba3 and XANTPHOS in the presence of excess Cs2CO3 afforded good yields of the coupled products. Subsequent reduction and cyclization of these intermediates provided the desired benzimidazole compounds.",

keywords = "Amination, Benzimidazoles, Catalysis, PLK, Palladium-catalyzed",

author = "Hornberger, {Keith R.} and Badiang, {Jennifer G.} and Salovich, {James M.} and Kuntz, {Kevin W.} and Emmitte, {Kyle A.} and Mui Cheung",

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doi = "10.1016/j.tetlet.2008.08.077",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Regioselective synthesis of benzimidazole thiophene inhibitors of polo-like kinase 1

AU - Hornberger, Keith R.

AU - Badiang, Jennifer G.

AU - Salovich, James M.

AU - Kuntz, Kevin W.

AU - Emmitte, Kyle A.

AU - Cheung, Mui

PY - 2008/10/27

Y1 - 2008/10/27

N2 - A regioselective synthesis of novel 1-(2-thienyl)-benzimidazole inhibitors of polo-like kinase 1 is described. Amination of substituted 2-iodo or -bromo nitrobenzenes with a 2-aminothiophene derivative catalyzed by Pd2dba3 and XANTPHOS in the presence of excess Cs2CO3 afforded good yields of the coupled products. Subsequent reduction and cyclization of these intermediates provided the desired benzimidazole compounds.

AB - A regioselective synthesis of novel 1-(2-thienyl)-benzimidazole inhibitors of polo-like kinase 1 is described. Amination of substituted 2-iodo or -bromo nitrobenzenes with a 2-aminothiophene derivative catalyzed by Pd2dba3 and XANTPHOS in the presence of excess Cs2CO3 afforded good yields of the coupled products. Subsequent reduction and cyclization of these intermediates provided the desired benzimidazole compounds.

KW - Amination

KW - Benzimidazoles

KW - Catalysis

KW - PLK

KW - Palladium-catalyzed

UR - http://www.scopus.com/inward/record.url?scp=51549109898&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2008.08.077

DO - 10.1016/j.tetlet.2008.08.077

M3 - Article

AN - SCOPUS:51549109898

SN - 0040-4039

VL - 49

SP - 6348

EP - 6351

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

Regioselective synthesis of benzimidazole thiophene inhibitors of polo-like kinase 1

Abstract

Keywords

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