Sequential Sonogashira and Suzuki cross-coupling reactions in the indole and indazole series

Synthesis

Volumn , Issue 5, 2005, Pages 771-780

  Witulski, Bernhard ^a   Azcon, Javier Ramon ^c   Alayrac, Carole ^a   Arnautu, Anca ^b   Collot, Valérie ^b   Rault, Sylvain ^b  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b CENTRE D ETUDES ET DE RECHERCHE SUR LE MÉDICAMENT DE NORMANDIE   (France)

^c NONE

Author keywords

Alkynes; Catalysis; Indazoles; Indoles; Palladium

Indexed keywords

CATALYSIS; PALLADIUM;

IODOINOLES; SEQUENTIAL CROSS-COUPLING REACTIONS; SONOGASHIRA CROSS-COUPLING REACTIONS; SUZUKI CROSS-COUPLING REACITONS;

ALCOHOLS;

3 IODOINDOLE DERIVATIVE; 5 BROMO 3 IODOINDAZOLE DERIVATIVE; 5 BROMO 3 IODOINDOLE DERIVATIVE; INDAZOLE DERIVATIVE; INDOLE DERIVATIVE; PALLADIUM; SEROTONIN RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; NEUROTRANSMISSION; REACTION ANALYSIS; SONOGASHIRA REACTION; SUZUKI REACTION; SYNTHESIS;

EID: 17144410349     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-861825     Document Type: Article

References (62)

1. (a) Hoyer, D.; Hannon, J. P.; Martin, G. R. Pharmacol. Biochem. Behav. 2002, 71, 533.
2. (b) Barnes, N. M.; Sharp, T. Neuropharmacology 1999, 38, 1083.
3. von Bohlen und Halbach, O.; Dermietzel, R. Neurotransmitters and Neuromodulators; Wiley-VCH: Weinheim, 2002, 107-115.
4. 7 receptors, see: Glennon, R. A. J. Med. Chem. 2003, 46, 2795.
5. (a) Tsai, Y.; Dukat, M.; Slassi, A.; MacLean, N.; Demchyshyn, L.; Savage, J. E.; Roth, B. L.; Hufesein, S.; Lee, M.; Glennon, R. A. Bioorg. Med. Chem. Lett. 2000, 10, 2295.
6. (b) Glennon, R. A.; Lee, M.; Rangisetty, J. B.; Dukat, M.; Roth, B. L.; Savage, J. E.; McBride, A.; Rauser, L.; Hufeisen, S.; Lee, D. K. H. J. Med. Chem. 2000, 43, 1011.
7. (c) Bromidge, S. M.; Brown, A. M.; Clark, S. E.; Dodgson, K.; Gager, T.; Grassam, H. L.; Jeffrey, P. M.; Joiner, G. F.; King, F. D.; Middlemiss, D. N.; Moss, S. F.; Newman, H.; Riley, G.; Routledge, C.; Wyman, P. J. Med. Chem. 1999, 42, 202.
8. (d) Sleight, A. J.; Boess, F. G.; Bös, M.; Levet-Trafit, B.; Riemer, C.; Bourson, A. Br. J. Pharmacol. 1998, 124, 556.
9. (a) Witulski, B.; Alayrac, C.; Tevzadze-Saeftel, L. Angew. Chem. Int. Ed. 2003, 42, 4257; Angew. Chem. 2003, 115, 4392.
10. (a) Witulski, B.; Alayrac, C.; Tevzadze-Saeftel, L. Angew. Chem. Int. Ed. 2003, 42, 4257; Angew. Chem. 2003, 115, 4392.
11. (b) Witulski, B.; Stengel, T. Angew. Chem. Int. Ed. 1998, 37, 489; Angew. Chem. 1998, 110, 495.
12. (b) Witulski, B.; Stengel, T. Angew. Chem. Int. Ed. 1998, 37, 489; Angew. Chem. 1998, 110, 495.
13. Witulski, B.; Alayrac, C. Angew. Chem. Int. Ed. 2002, 41, 3281; Angew. Chem. 2002, 114, 3415.
14. Witulski, B.; Alayrac, C. Angew. Chem. Int. Ed. 2002, 41, 3281; Angew. Chem. 2002, 114, 3415.
15. (a) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry, Tetrahedron Organic Chemistry Series, Vol. 20; Pergamon: Oxford, 2000.
16. (b) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
17. (c) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1998.
18. (a) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, P.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 203-229.
19. (b) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
20. (c) Sonogashira, K. In Comprehensive Organic Syntheses, Vol. 3; Trost, B.; Fleming, I., Eds.; Pergamon Press: New York, 1991, 521-549.
21. (a) Suzuki, A. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, 2002, 53-106.
22. (b) Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 207.
23. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
24. (a) For sequential Stille and Heck cross-coupling reactions towards 3,4-diallyl indoles, see: Brown, M. A.; Kerr, M. A. Tetrahedron Lett. 2001, 42, 983.
25. (b) For combined N- and C-arylations with boronic acids in the indazole series, see: Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron Lett. 2000, 41, 9053.
26. (c) For the synthesis of 3,5-diaryl indoles via tandem Pd-promoted cross coupling reactions, see: Yang, Y.; Martin, A. R. Synth. Commun. 1992, 22, 1757.
27. (d) For sequential multi Pd-catalyzed cross-coupling reactions in benzofuran series, see: Bach, T.; Bartels, M. Synlett 2001, 1284.
28. (e) Bach, T.; Bartels, M. Synthesis 2003, 925.
29. For Suzuki and Sonogashira reactions with aryl chlorides, see: (a) Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290; Angew. Chem. 2002, 114, 1342.
30. For Suzuki and Sonogashira reactions with aryl chlorides, see: (a) Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290; Angew. Chem. 2002, 114, 1342.
31. (b) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176; Angew. Chem. 2002, 114, 4350.
32. (b) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176; Angew. Chem. 2002, 114, 4350.
33. (c) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem. Int. Ed. 2003, 42, 1056; Angew. Chem. 2003, 115, 1086.
34. (c) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem. Int. Ed. 2003, 42, 1056; Angew. Chem. 2003, 115, 1086.
35. (d) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem. Int. Ed. 2004, 43, 1871; Angew. Chem. 2004, 116, 1907.
36. (d) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem. Int. Ed. 2004, 43, 1871; Angew. Chem. 2004, 116, 1907.
37. (e) Gelman, D.; Buchwald, S. L. Angew. Chem. Int. Ed. 2003, 43, 5993; Angew. Chem. 2003, 115, 6175.
38. (e) Gelman, D.; Buchwald, S. L. Angew. Chem. Int. Ed. 2003, 43, 5993; Angew. Chem. 2003, 115, 6175.
39. (a) Arnautu, A.; Collot, V.; Calvo Ros, J.; Alayrac, C.; Wituski, B.; Rault, S. Tetrahedron Lett. 2002, 43, 2695.
40. (b) Collot, V.; Dallemagne, P.; Bovy, P. R.; Rault, S. Tetrahedron 1999, 55, 6917.
41. For other recent work on the functionalisation of indazoles in position 3, see: (a) Yang, Y.; Knochel, P. Synlett 2004, 2303.
42. (b) Hari, Y.; Shoji, Y.; Aoyama, T. Synthesis 2004, 1183.
43. (c) Gordon, D. W. Synlett 1998, 1065.
44. (d) Welch, W. M.; Hanau, C. E.; Whalen, W. M. Synthesis 1992, 937.
45. (a) Harrington, P. J.; Hegedus, L. S.; McDaniel, K. F. J. Am. Chem. Soc. 1987, 109, 4335.
46. (b) Hegedus, L. S.; Sestrick, M. R.; Michaelson, E. T.; Harrington, P. J. J. Org. Chem. 1989, 54, 4141.
47. (c) Merlic, C. A.; Semmelhack, M. F. J. Organomet. Chem. 1990, 391, C23.
48. (d) Bando, T.; Shishido, K. Heterocycles 1997, 46, 111.
49. For the synthesis of 3-alkynyl indoles by palladium catalysed Stille reactions, see: (a) Sakamoto, T.; Yasuhara, A.; Kondo, Y.; Yamanaka, H. Synlett 1992, 502.
50. (b) Kanekiyo, N.; Kuwada, T.; Choshi, T.; Nobuhiro, J.; Hibino, S. J. Org. Chem. 2001, 66, 8793.
51. (a) Sakamoto, T.; Ohsawa, K. J. Chem. Soc., Perkin Trans. 1 1999, 2323.
52. (b) Jiang, B.; Kan, Y.; Zhang, A. Tetrahedron 2001, 57, 1581.
53. Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 2248.
54. Witulski, B.; Buschmann, N.; Bergsträßer, U. Tetrahedron 2000, 56, 8473.
55. Papanastassiou, Z. B.; Bruni, R. J.; White, E. J. Med. Chem. 1967, 10, 701.
56. (a) Yoneda, N.; Matsuoka, S.; Miyaura, N.; Fukuhara, T.; Suzuki, A. Bull. Chem. Soc. Jpn. 1990, 63, 2124.
57. (b) Sakamoto, T.; Shiga, F.; Yasuhara, A.; Uchiyama, D.; Kondo, Y.; Yamanaka, H. Synthesis 1992, 746.
58. (c) Kundu, N. G.; Dasgupta, S. K. J. Chem. Soc., Perkin Trans. 1 1993, 2657.
59. For examples of Sonogashira couplings between electron deficient alkynes and diaryliodonium salts, see: Radhakrishnan, U.; Stang, P. J. Org. Lett. 2001, 3, 859.
60. Lynne, A. H.; Koenig, T. M.; Ginah, F. O.; Copp, J. D.; Mitchell, D. J. Org. Chem. 1998, 63, 5050.
61. 3 as catalyst have been reported, see: Hundertmark, T.; Linke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729.
62. (b) In our hands, application of this protocol to our substrates has not been satisfactory so far.