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Synthesis 2015; 47(20): 3169-3178
DOI: 10.1055/s-0034-1381040
DOI: 10.1055/s-0034-1381040
paper
Preparation of 2,3-Disubstituted 5-Bromo-1H-pyrrolo[2,3-b]pyridine Framework by Fischer Cyclization
Further Information
Publication History
Received: 18 April 2015
Accepted after revision: 14 May 2015
Publication Date:
15 July 2015 (online)
Abstract
A simple synthesis of some hard-to-reach heterocycles containing 2,3-disubstituted 5-bromo-1H-pyrrolo[2,3-b]pyridine framework by Fisсher indole cyclization in polyphosphoric acid has been developed. A particularly valuable feature of this synthetic route is the possibility to build a 5-bromo-7-azaindole scaffold with alkyl or aryl substituents at positions 2 and 3 from available starting materials.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1381040.
- Supporting Information
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References
- 1a Mérour J.-Y, Buron F, Plé K, Bonnet P, Routier S. Molecules 2014; 19: 19935
- 1b Mérour J.-Y, Routier S, Suzenet F, Joseph B. Tetrahedron 2013; 69: 4767
- 2a Ahaidar A, Fernández D, Danelón G, Cuevas C, Manzanares I, Albericio F, Joule JA, Alvarez M. J. Org. Chem. 2003; 68: 10020
- 2b Choshi T, Yamada S, Sugino E, Kuwada T, Hibino S. J. Org. Chem. 1995; 60: 5899
- 3a Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893
- 3b De Sá Alves FR, Barreiro EJ, Fraga CA. M. Mini Rev. Med. Chem. 2009; 9: 782
- 3c Sharma V, Kumar P, Pathak D. J. Heterocycl. Chem. 2010; 47: 491
- 3d Welsch ME, Snyder SA, Stockwell BR. Curr. Opin. Chem. Biol. 2010; 14: 347
- 4a Perry NB, Ettouati L, Litaudon M, Blunt JW, Munro MH. G, Parkin S, Hope H. Tetrahedron 1994; 50: 3987
- 4b Walker SR, Carter EJ, Huff BC, Morris JC. Chem. Rev. 2009; 109: 3080
- 5 Mérour J.-Y, Joseph B. Curr. Org. Chem. 2001; 5: 471
- 6a Song JJ, Reeves JT, Gallou F, Tan Z, Yee NK, Senanayake CH. Chem. Soc. Rev. 2007; 1120
- 6b Sun L.-P, Huang X.-H, Wang J.-X. J. Chin. Chem. Soc. 2007; 54: 569
- 7 Popowycz F, Routier S, Joseph B, Mérour J-Y. Tetrahedron 2007; 63: 1031
- 8a Okuda S, Robison MM. J. Am. Chem. Soc. 1959; 81: 740
- 8b Kelly AH, Parrick J. Can. J. Chem. 1966; 44: 2455
- 8c Herbert C, Wibberley DG. J. Chem. Soc. C 1969; 1505
- 8d Alekseyev RS, Amirova SR, Kabanova EV, Terenin VI. Chem. Heterocycl. Compd. 2014; 50: 1305
- 9a Jeanty M, Blu J, Suzenet F, Guillaumet G. Org. Lett. 2009; 11: 5142
- 9b Thomae D, Jeanty M, Coste J, Guillaumet G, Suzenet F. Eur. J. Org. Chem. 2013; 3328
- 10a Gummadi VR, Rajagopalan S, Yeng LC, Paydar M, Renukappa GA, Ainan BR, Krishnamurthy NR, Panigrahi SK, Mahasweta K, Raghuramachandran S, Rajappa M, Ramanathan A, Lakshminarasimhan A, Ramachandra M, Fong WP, Mustafa MR, Nanduri S, Hosahalli S. Bioorg. Med. Chem. Lett. 2013; 23: 4911
- 10b Hong S, Lee S, Kim B, Lee H, Hong S.-S, Hong S. Bioorg. Med. Chem. Lett. 2010; 20: 7212
- 10c Gourdain S, Dairou J, Denhez C, Bui LC, Rodrigues-Lima F, Janel N, Delabar JM, Cariou K, Dodd RH. J. Med. Chem. 2013; 56: 9569
- 10d Hong S, Kim J, Seo JH, Jung KH, Hong S.-S, Hong S. J. Med. Chem. 2012; 55: 5337
- 10e McCoull W, Hennessy EJ, Blades K, Box MR, Chuaqui C, Dowling JE, Davies CD, Ferguson AD, Goldberg FW, Howe NJ, Kemmitt PD, Lamont GM, Madden K, McWhirter C, Varnes JG, Ward RA, Williams JD, Yang B. Med. Chem. Commun. 2014; 5: 1533
- 11 Guillard J, Larraya C, Viaud-Massuard MC. Heterocycles 2003; 60: 865
- 12a Kroth H, Hamel C, Benderitter P, Froestl W, Sreenivasachary N, Muhs A. US Patent 2011/0280808, 2011
- 12b Aadal Nielsen P, Brimert T, Kristoffersson A, Linnanen T, Sjö P. Patent WO 2004/016609, 2004
- 12c Briving C, Carlsson S, Carter R, Elebring M, Kuehler T, Nordberg P, Starke I, Svensson A. US Patent 5439917, 1995
- 12d Ohtsuka M, Haginoya N, Ichikawa M, Matsunaga H, Saito H, Shibata Y, Tsunemi Y. US Patent 2011/0082138, 2011
- 13 Lachance N, Chan WY. J. Heterocycl. Chem. 2003; 40: 289
- 14a Pillard C, Basséne CE, Suzenet F, Guillaumet G. Synthesis 2008; 2049
- 14b Lachance N, April M, Joly M.-A. Synthesis 2005; 2571
- 15 Yakhontov LN, Pronina EV. Zh. Org. Khim. 1968; 4: 1675 ; Chem. Abstr. 1969, 70, 3869w
- 16 Alekseyev RS, Kurkin AV, Yurovskaya MA. Chem. Heterocycl. Compd. 2011; 47: 584
- 17 Fox BA, Threlfall TL. Org. Synth. 1964; 44: 34
- 18 Paudler WW, Jovanovic MV. J. Org. Chem. 1983; 48: 1064
- 19 Case FH. J. Am. Chem. Soc. 1946; 68: 2574
- 20 Moran DB, Morton GO, Albright JD. J. Heterocycl. Chem. 1986; 23: 1071
- 21 Uhlig F. Angew. Chem. 1954; 66: 435