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http://dx.doi.org/10.5012/bkcs.2014.35.7.1970

A Facile and Efficient Synthesis of Dronedarone Hydrochloride  

Li, Feng (School of Biological & Chemical Engineering, Ningbo Institute of Technology, Zhejiang University)
Jin, Chunhua (School of Biological & Chemical Engineering, Ningbo Institute of Technology, Zhejiang University)
Zou, Jianwei (School of Biological & Chemical Engineering, Ningbo Institute of Technology, Zhejiang University)
Wu, Jun (Department of Chemistry, Zhejiang University)
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Abstract
A facile and efficient synthesis of dronedarone hydrochloride starting from commercially available 4-nitrophenol is described. This approach features a tandem-type synthesis of 3-carbonylated benzofuran involving cyclization of 2-ethynylphenol followed by $CO_2$ fixation at the 3-position of the benzofuran ring mediated by potassium carbonate without the addition of any transition metal catalyst.
Keywords
Dronedarone; Tandem-type synthesis; Cyclization; $CO_2$ fixation;
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1 Fu, H. Q.; Yang, T. B.; Zhao, M. X. CN 101993427 B, 2009.
2 Atta, A. K.; Kim, S. B.; Heo, J.; Cho, D. G. Org. Lett. 2013, 15, 1072.   DOI   ScienceOn
3 Inamoto, K.; Asano, N.; Nakamura, Y.; Yonemoto, M.; Kondo, Y. Org. Lett. 2012, 14, 2622.   DOI   ScienceOn
4 Eklund, L. WO 2009044143 A2, 2008.
5 Friesz, A.; Dombrady, Z.; Csatarine, N. M. WO 2011070380 A1, 2010.
6 Friesz, A.; Csatarinenagy, M. WO 2011083346 A1, 2010.
7 Zhai, F. M.; Chen, Y. J.; Hu, Q. CN 102180848 A, 2010.
8 Sada, M.; Nardi, A.; Maiorana, S. WO 2011104591 A1, 2011.
9 Giri, R. L.; Mohite, V. D.; Kambhampati, S.; Chitturi, T. R.; Thennati, R. Org. Process Res. Dev. 2012, 16, 677.   DOI   ScienceOn
10 Grimaud, B.; Grossi, P. J. WO 2012127173 A1, 2012.
11 Ju, L.; Zou, J.; Yang, Y.; Wang, W. F.; Liu, Y. X. CN 102321058 A, 2012.
12 Gong, Q. C.; Si, Z. X. CN 102675267 A, 2012.
13 Friesz, A.; Dombrady, Z. WO 2013014479 A1, 2013.
14 Richter, F.; Schreiner, E.; Pirc, S.; Copar, A. WO 2012062918 A1, 2011.
15 Brenans, P. Bull. Soc. Chim. Fr. 1902, 27, 398.
16 Shoutteeten, A.; Bleger, F.; Mordacq, F.; Piron, J. WO 2005066149 A1, 2004.
17 Dobromir, D.; Stanley, N. Lancet 2010, 375, 1212.   DOI   ScienceOn
18 Kuzniatsova, N.; Pamukcu, B.; Lip, G. Y. H. Therapy 2011, 8, 681.   DOI   ScienceOn
19 Patel, P. B.; Patel, K. C.; Mehta, H. R. Int. Res. J. Pharm. 2011, 2, 59.
20 Patel, P. D.; Bhuriya, R.; Patel, D. D.; Arora, B. L.; Singh, P. P.; Arora, R. R. Vasc. Health Risk Manage 2011, 5, 635.
21 Singh, B. N.; Capucci, A.; Radzik, D.; Hohnloser, S. N. Engl. J. Med. 2007, 357, 987.   DOI   ScienceOn
22 Gubin, J.; Lucchetti, J.; Inion, H.; Chatelain, P.; Rosseels, G.; Kilenyi, S. EP 0471609 A1, 1991.
23 Biard, M. WO 2002048078 A1, 2001.
24 Fino, N.; Leroy, C. WO 2002048132 A1, 2001.
25 Rozhikov, R. V.; Larock, R. C. J. Org. Chem. 2010, 75, 4131.   DOI   ScienceOn
26 Gutman, A.; Nisnevich, G.; Yudovitch, L. WO 2003040120 A1, 2003.
27 Friesz, A.; Dombrady, Z.; Csatarine, N. M.; Huszar, C. WO 2013014480 A1, 2013.
28 Li, F.; Tian, S. H.; Song, X. F.; Li, W. Y.; Cheng, H. Y.; Lei, L. Z.; Zhu, Q. F.; Jin, C. H.; Li, S. H. Chem. J. Chinese Universities 2013, 34, 858.