Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2011(1): 45-50
DOI: 10.1055/s-0030-1258971
DOI: 10.1055/s-0030-1258971
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkPyrrole Acylation for the Synthesis of 2-Bromo-6-(2-pyrrolyl)pyridine and Subsequent Cross-Coupling Reactions
Further Information
Received
21 September 2010
Publication Date:
09 November 2010 (online)
Publication History
Publication Date:
09 November 2010 (online)
Abstract
A facile synthesis of 2-bromo-6-pyrrolylpyridine 4 was developed starting from acylation of pyrrole with glutaric acid and TFAA. Suzuki cross-couplings of 4 with arylboronic acids gave a variety of novel 2-aryl-6-pyrrolylpyridines in excellent yields.
Key words
pyrrole acylation - 2-bromo-6-pyrrolylpyridine - 2-aryl-6-pyrrolylpyridines - Suzuki cross-coupling - detosylation
- Supporting Information for this article is available online:
- Supporting Information
- 1a
Schmidtke SJ.MacManus-Spencer LA.Klappa JJ.Mobley TA.McNeil K.Blank DA. Phys. Chem. Chem. Phys. 2004, 6: 3938MissingFormLabel - 1b
MacManus-Spencer LA.Schmidtke SJ.Blank DA.McNeil K. Phys. Chem. Chem. Phys. 2004, 6: 3948MissingFormLabel - 2
Trofimov BA.Vasil’tsov AM.Schmidt EYu.Zorina NV.Afonin AV.Mikhaleva AI.Petrushenko KB.Ushakov IA.Krivdin LB.Belsky VK.Bryukvina LI. Eur. J. Org. Chem. 2005, 4338 - 3
Jones RA.Karatza M.Voro TN.Civcir PU.Franck A.Ozturk O.Seaman JP.Whitmore AP.Williamson DJ. Tetrahedron 1996, 52: 8707 ; and references cited therein - 4
Wang H.Zeng Y.Ma JS.Fu H.Yao J.Mikhaleva AI.Trofimov BA. Chem. Commun. 2009, 5457 - 5
Pucci D.Aiello I.Aprea A.Bellusci A.Crispini A.Ghedini M. Chem. Commun. 2009, 1550 - 6
Chen J.-L.Lin C.-H.Chen J.-H.Chi Y.Chiu Y.-C.Chou P.-T.Lai C.-H.Lee G.-H.Carty AJ. Inorg. Chem. 2008, 47: 5154 - 7a
Luedtke AT.Goldberg KI. Inorg. Chem. 2007, 46: 8496MissingFormLabel - 7b
Luedtke AT.Goldberg KI. Angew. Chem. Int. Ed. 2008, 47: 7694MissingFormLabel - 8
McBee JL.Tilley TD. Organometallics 2010, 29: 184 - 9
Ciszek JW.Keane ZK.Cheng L.Stewart MP.Yu LH.Natelson D.Tour JM. J. Am. Chem. Soc. 2006, 128: 3179 - 10
Schouteeten S.Allen OR.Haley AD.Ong GL.Jones GD.Vicic DA. J. Organomet. Chem. 2006, 691: 4975 - 11
Nagata T.Tanaka K. Bull. Chem. Soc. Jpn. 2002, 75: 2469 - 12
Klappa JJ.Geers SA.Schmidtke SJ.MacManus-Spencer LA.McNeil K. Dalton Trans. 2004, 883 - 13
Setsune J.-I.Watanabe K. J. Am. Chem. Soc. 2008, 130: 2404 - For other related systems as ligands, see:
- 14a
Wu F.Chamchoumis CM.Thummel RP. Inorg. Chem. 2000, 39: 584MissingFormLabel - 14b
Liu SF.Wu Q.Schmider HL.Aziz H.Hu NX.Popovic Z.Wang S. J. Am. Chem. Soc. 2000, 122: 3671MissingFormLabel - 14c
Corriu RJP.Bolin G.Moreau JJE.Vernhet C. J. Chem. Soc., Chem. Commun. 1991, 211MissingFormLabel - 14d
Carré FH.Corriu RJP.Bolin G.Moreau JJE.Vernhet C. Organometallics 1993, 12: 2478MissingFormLabel - 15
Lehuédé J.Fauconneau B.Barrier L.Ourakow M.Piriou A.Vierfond J.-M. Eur. J. Med. Chem. 1999, 34: 991 - 16
de Laszlo SE.Visco D.Agarwal L.Chang L.Chin J.Croft G.Forsyth A.Fletcher D.Frantz B.Hacker C.Hanlon W.Harper C.Kostura M.Li B.Luell S.MacCoss M.Mantlo N.O’Neill EA.Orevillo C.Pang M.Parsons J.Rolando A.Sahly Y.Sidler K.Widmer WR.O’Keefe SJ. Bioorg. Med. Chem. Lett. 1998, 8: 2689 - 17
Dowell RI.Hales NJ.Tucker H. Eur. J. Med. Chem. 1993, 28: 513 - 18
Setsune J.-i.Toda M.Watanabe K.Panda PK.Yoshida T. Tetrahedron 2006, 47: 7541 - 19
Kudo N.Perseghini M.Fu GC. Angew. Chem. Int. Ed. 2006, 45: 1282MissingFormLabel - 20a
Seggio A.Priem G.Cheuallier F.Mongin F. Synthesis 2009, 3617MissingFormLabel - 20b
Seggio A.Jutand A.Priem G.Mongin F. Synlett 2008, 2955MissingFormLabel - 21
Annunziata L.Pappalardo D.Tedesco C.Pellecchia C. Macromolecules 2009, 42: 5572 - 22
Semmelhack MF.Chlenov A.Ho DM. J. Am. Chem. Soc. 2005, 127: 7759 - 23
Dinsmore A.Billing DG.Mandy K.Michael JP.Mogano D.Patil S. Org. Lett. 2004, 6: 293 - 24
García-Cuadrado D.Cuadro AM.Alvarez-Buillia J.Vaquero JJ. Synlett 2002, 1904 - 25
Seki K.-i.Ohkura K.Terashima M. Heterocycles 1984, 22: 2347 - 26
Shiao M.-J.Shih L.-H.Chia W.-L.Chau T.-Y. Heterocycles 1991, 32: 2111 - 27
Klappa JJ.Rich AE.McNeill K. Org. Lett. 2002, 4: 435 - 28
Hansford KA.Guarin SAP.Skene WG.Lubell WD. J. Org. Chem. 2005, 70: 7996 - 29
Savoia D.Concialini V.Roffia S.Tarsi L. J. Org. Chem. 1991, 56: 1822 - 30
Lucchesini F. Tetrahedron 1992, 48: 9951 - 31
Siriwardana AI.Kathriarachchi KKADS.Nakamura I.Gridnev ID.Yamamoto Y. J. Am. Chem. Soc. 2004, 126: 13898 - 32
Romashin YN.Liu MTH.Ma W.Moss RA. Tetrahedron Lett. 1999, 40: 7163 - 33
von der Saal W.Reinhardt R.Stawitz J.Quast H. Eur. J. Org. Chem. 1998, 1645 - 34
Mullen GB.Georgiev VSt. J. Org. Chem. 1989, 54: 2476 - 35
Mantri M.de Graaf O.van Veldhoven J.Göblyös A.von Frijtag Drabbe Künzel JK.Mulder-Krieger T.Link R.de Vries H.Beukers MW.Brussee J.IJzerman AP. J. Med. Chem. 2008, 51: 4449 - 36
Wang Y.-F.Chiba S. J. Am. Chem. Soc. 2009, 131: 12570 - 37 For a review of pyridine synthesis,
see:
Henry GD. Tetrahedron 2004, 60: 6043MissingFormLabel - 38a
Song C.Knight DW.Whatton MA. Tetrahedron Lett. 2004, 45: 9573MissingFormLabel - 38b
Song C.Knight DW.Whatton MA. Org. Lett. 2006, 8: 163MissingFormLabel - 39
Song C.Zhao P.Liu Y.Liu H.Li W.Shi S.Chang J. Tetrahedron 2010, 66: 5378 - 40
Janosik T.Shirani H.WahlstrÖm N.Malky I.Stensland B.Bergman J. Tetrahedron 2006, 62: 1699 - 41
Coe JW. Org. Lett. 2000, 2: 4205 - 42
Stead D.O’Brien P.Sanderson AJ. Org. Lett. 2005, 7: 4459 - 43
Stevenson L.Pimlott SL.Sutherland A. Tetrahedron Lett. 2007, 48: 7137 - 44
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457MissingFormLabel