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Synlett 2012; 23(15): 2279-2283
DOI: 10.1055/s-0031-1290456
DOI: 10.1055/s-0031-1290456
letter
100 Gram Scale Synthesis of a Key Intermediate of Matrix Metalloproteinase Inhibitor in a Continuous-Flow System Based on a Copper-Free Sonogashira Reaction Using an Ionic Liquid as a Catalyst Support
Weitere Informationen
Publikationsverlauf
Received: 30. Mai 2012
Accepted after revision: 28. Juni 2012
Publikationsdatum:
14. August 2012 (online)
Abstract
The key intermediate of matrix metalloproteinase (MMP) inhibitor was synthesized using a flow microreactor for a copper-free Sonogashira coupling reaction in an ionic liquid. The ionic liquid [emim]NTf2 was used as a solvent and a catalyst support. A 100 g scale synthesis was achieved in combination with a flow-extraction/catalyst-recycling system, in which the ionic liquid containing the palladium catalyst was continuously recycled.
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References
- 1a Wirth T. Microreactors in Organic Synthesis and Catalysis. Wiley-VCH; Weinheim: 2008
- 1b Hessel V, Renken A, Schouten JC, Yoshida J.-I. Micro Process Engineering . Wiley-VCH; Weinheim: 2009
-
1c Mason BP, Price KE, Steinbacher JL, Bogdan AR, McQuade DT. Chem. Rev. 2007; 107: 2300
- 1d Yoshida J, Nagaki A, Yamada T. Chem.–Eur. J. 2008; 14: 7450
- 1e Lin W.-Y, Wang Y, Wang S, Tseng H.-R. Nano Today 2009; 4: 470
- 1f McMullen JP, Jensen KF. Annu. Rev. Anal. Chem. 2010; 3: 19
- 1g Webb D, Jamison TF. Chem. Sci. 2010; 675
- 1h Yoshida J. Chem. Rec. 2010; 10: 332
-
1i Wegner J, Ceylan S, Kirschning A. Chem. Commun. 2011; 47: 4583
- 2 For a review of our work, see: Fukuyama T, Rahman MT, Sato M, Ryu I. Synlett 2008; 151
- 3a Hessel V, Hofmann C, Löwe H, Meudt A, Scheres S, Schönfeld F, Werner B. Org. Process Res. Dev. 2004; 8: 511
- 3b Wakami H, Yoshida J. Org. Process Res. Dev. 2005; 9: 787
- 3c Iwasaki T, Kawano N, Yoshida J. Org. Process Res. Dev. 2006; 10: 1126
- 3d Tanaka K, Motomatsu S, Koyama K, Tanaka S, Fukase K. Org. Lett. 2007; 9: 299
- 4 Tamura Y, Watanabe F, Nakatani T, Yasui K, Fuji M, Komurasaki T, Tsuzuki H, Maekawa R, Yoshioka T, Kawada K, Sugita K, Ohtani M. J. Med. Chem. 1998; 41: 640
- 5 Sugimoto A, Fukuyama T, Rahman MT, Ryu I. Tetrahedron Lett. 2009; 50: 6364
- 6 Fukuyama T, Shinmen M, Nishitani S, Sato M, Ryu I. Org. Lett. 2002; 4: 1691
- 7 Liu S, Fukuyama T, Sato M, Ryu I. Org. Process Res. Dev. 2004; 8: 477
- 8 Rahman MT, Fukuyama T, Kamata N, Sato M, Ryu I. Chem. Commun. 2006; 2236
- 9a Wasserscheid P, Welton T. Ionic Liquids in Synthesis . Wiley-VCH; Weinheim: 2008
- 9b Ranke J, Stolte S, Störmann R, Arning J, Jastorff B. Chem. Rev. 2007; 107, 21: 83
- 9c Plechkova NV, Seddon KR. Chem. Soc. Rev. 2008; 37: 123
- 9d Hallett JP, Welton T. Chem. Rev. 2011; 111: 3508
- 9e Isambert N, del Mar Sanchez Duque M, Plaquevent J.-C, Génisson Y, Rodriguez J, Constantieux T. Chem. Soc. Rev. 2011; 40: 1347
- 9f Petkovic M, Seddon KR, Rebelo LP. N, Pereira CS. Chem. Soc. Rev. 2011; 40: 1383
- 10a Liu SF, Fukuyama T, Sato M. Synlett 2004; 1814
- 10b Fukuyama T, Yamaura R, Ryu I. Can. J. Chem. 2005; 83: 711
- 10c Rahman MT, Fukuyama T, Ryu I, Suzuki K, Yonemura K, Hughes PF, Nokihara K. Tetrahedron Lett. 2006; 47: 2703
- 10d Fukuyama T, Inouye T, Ryu I. J. Organomet. Chem. 2007; 692: 685
- 10e Fukuyama T, Rahman MT, Maetani S, Ryu I. Chem. Lett. 2011; 40: 1027
For selected examples, see:
For recent reviews, see:
For our reports on coupling reactions using ionic liquids, see: