Palladium-Catalyzed N-Arylation of 2-Aminothiazoles

作者: Meredeth A. McGowan , Jaclyn L. Henderson , Stephen L. Buchwald

DOI: 10.1021/OL300178J

关键词:

摘要: A method for the Pd-catalyzed coupling of 2-aminothiazole derivatives with aryl bromides and triflates is described. Significantly, this class nucleophiles, exhibits a broad substrate scope proceeds reasonable catalyst loading. Furthermore, an interesting effect acetic acid as additive uncovered that facilitates activation.

参考文章(25)
Maria Z Kounnas, Anne M Danks, Soan Cheng, Curtis Tyree, Elizabeth Ackerman, Xulun Zhang, Kwangwook Ahn, Phuong Nguyen, Dan Comer, Long Mao, Chengzhi Yu, David Pleynet, Paul J Digregorio, Gonul Velicelebi, Kenneth A Stauderman, William T Comer, William C Mobley, Yue-Ming Li, Sangram S Sisodia, Rudolph E Tanzi, Steven L Wagner, None, Modulation of γ-Secretase Reduces β-Amyloid Deposition in a Transgenic Mouse Model of Alzheimer's Disease Neuron. ,vol. 67, pp. 769- 780 ,(2010) , 10.1016/J.NEURON.2010.08.018
Yan Lu, Chien-Ming Li, Zhao Wang, Jianjun Chen, Michael L. Mohler, Wei Li, James T. Dalton, Duane D. Miller, Design, Synthesis, and SAR Studies of 4-Substituted Methoxylbenzoyl-aryl-thiazoles Analogues as Potent and Orally Bioavailable Anticancer Agents Journal of Medicinal Chemistry. ,vol. 54, pp. 4678- 4693 ,(2011) , 10.1021/JM2003427
Robert M. Borzilleri, Rajeev S. Bhide, Joel C. Barrish, Celia J. D'Arienzo, George M. Derbin, Joseph Fargnoli, John T. Hunt, Robert Jeyaseelan, Amrita Kamath, Daniel W. Kukral, Punit Marathe, Steve Mortillo, Ligang Qian, John S. Tokarski, Barri S. Wautlet, Xiaoping Zheng, Louis J. Lombardo, Discovery and evaluation of N-cyclopropyl- 2,4-difluoro-5-((2-(pyridin-2-ylamino)thiazol-5- ylmethyl)amino)benzamide (BMS-605541), a selective and orally efficacious inhibitor of vascular endothelial growth factor receptor-2. Journal of Medicinal Chemistry. ,vol. 49, pp. 3766- 3769 ,(2006) , 10.1021/JM060347Y
Yifeng Liu, Yajun Bai, Juan Zhang, Yangyang Li, Junping Jiao, Xiaoli Qi, Optimization of the Conditions for Copper‐Mediated N‐Arylation of Heteroarylamines European Journal of Organic Chemistry. ,vol. 2007, pp. 6084- 6088 ,(2007) , 10.1002/EJOC.200700577
Debabrata Maiti, Brett P. Fors, Jaclyn L. Henderson, Yoshinori Nakamura, Stephen L. Buchwald, Palladium-Catalyzed Coupling of Functionalized Primary and Secondary Amines with Aryl and Heteroaryl Halides: Two Ligands Suffice in Most Cases Chemical Science. ,vol. 2, pp. 57- 68 ,(2011) , 10.1039/C0SC00330A
S. Giltaire, F. Herphelin, A. Frankart, M. Hérin, P. Stoppie, Y. Poumay, The CYP26 inhibitor R115866 potentiates the effects of all-trans retinoic acid on cultured human epidermal keratinocytes. British Journal of Dermatology. ,vol. 160, pp. 505- 513 ,(2009) , 10.1111/J.1365-2133.2008.08960.X
Jingjun Yin, Matthew M. Zhao, Mark A. Huffman, James M. McNamara, Pd-CatalyzedN-Arylation of Heteroarylamines Organic Letters. ,vol. 4, pp. 3481- 3484 ,(2002) , 10.1021/OL0265923
Brett P. Fors, Philipp Krattiger, Eric Strieter, Stephen L. Buchwald, Water-mediated catalyst preactivation: an efficient protocol for C-N cross-coupling reactions. Organic Letters. ,vol. 10, pp. 3505- 3508 ,(2008) , 10.1021/OL801285G
Tim H.M Jonckers, Bert U.W Maes, Guy L.F Lemière, Roger Dommisse, Selective palladium-catalyzed aminations on dichloropyridines Tetrahedron. ,vol. 57, pp. 7027- 7034 ,(2001) , 10.1016/S0040-4020(01)00659-7
Thomas J. Maimone, Phillip J. Milner, Tom Kinzel, Yong Zhang, Michael K. Takase, Stephen L. Buchwald, Evidence for in Situ Catalyst Modification during the Pd-Catalyzed Conversion of Aryl Triflates to Aryl Fluorides Journal of the American Chemical Society. ,vol. 133, pp. 18106- 18109 ,(2011) , 10.1021/JA208461K