A soluble base for the copper-catalyzed imidazole N-arylations with aryl halides

Journal of Organic Chemistry

Volumn 70, Issue 24, 2005, Pages 10135-10138

  Liu, Longbin ^a   Frohn, Mike ^a   Xi, Ning ^a   Dominguez, Celia ^a   Hungate, Randy ^a   Reider, Paul J ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COPPER; HALOGEN COMPOUNDS; MOLECULAR STRUCTURE; REACTION KINETICS; SOLUBILITY;

ARYL BROMIDES; LIGAND;

NITROGEN COMPOUNDS;

8 QUINOLINOL; CARBONIC ACID DERIVATIVE; COPPER; HALIDE; IMIDAZOLE; LIGAND; SOLVENT; TETRYLAMMONIUM; WATER;

AMIDATION; ARTICLE; ARYLATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; REACTION ANALYSIS; REACTION OPTIMIZATION; SOLUBILITY;

ALKYLATION; CATALYSIS; COPPER; HYDROCARBONS, HALOGENATED; IMIDAZOLES; MOLECULAR STRUCTURE; SOLUBILITY; STEREOISOMERISM;

EID: 28044443893     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051640t     Document Type: Article

References (75)

1. For reviews on Cu-catalyzed coupling reactions, see: (a) Lindley, J. Tetrahedron 1984, 40, 1433-1456.
2. (b) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449.
3. (c) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428-2439.
4. (d) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337-2364.
5. For recent examples of Cu-catalyzed N-arylations with aryl halides, see: (e) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428 and references therein.
6. (f) Okano, K.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2003, 5, 4987-4990.
7. (g) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793-796.
8. (h) He, H.; Wu, Y.-J. Tetrahedron Lett. 2003, 44, 3385-3386.
9. For examples of cAMP PDE inhibitor, see: (a) Venuti, M. C.; Stephenson, R. A.; Alvarez, R.; Bruno, J. J.; Strosberg, A. M. J. Med. Chem. 1988, 31, 2136-2145.
10. Thromboxane synthase inhibitor: (b) Martinez, G. R.; Walker, K. A. M.; Hirschfeld, D. R.; Bruno, J. J.; Yang, D. S.; Maloney, P. J. J. Med. Chem. 1992, 35, 620-628.
11. (c) Iizuka, K.; Akahane, K.; Momose, D.; Nakazawa, M. J. Med. Chem. 1981, 24, 1139-1148.
12. (d) Cozzi, P.; Carganico, G.; Fusar, D.; Grossoni, M.; Menichincheri, M.; Pinciroli, V.; Tonani, R.; Vaghi, F.; Salvati, P. J. Med. Chem. 1993, 36, 2964-2972.
13. (e) Qiao, J. X.; Cheng, X.; Modi, D. P.; Rossi, K. A.; Luettgen, J. M.; Knabb, R. M.; Jadhav, P. K.; Wexler, R. R. Bioorg. Med. Chem. Lett. 2005, 15, 29-35.
14. Angiotensin-II agonist: (f) Wan, Y.; Wallinder, C.; Plouffe, B.; Beaudry, H.; Mahalingam, A. K.; Wu, X.; Johansson, B.; Holm, M.; Botoros, M.; Karlen, A.; Pettersson, A.; Nyberg, F.; Faendriks, L.; Gallo-Payet, N.; Hallberg, A.; Alterman, M. J. Med. Chem. 2004, 47, 5995-6008.
15. Cardiotonic agent: (g) Sircar, I.; Weishaar, R. E.; Kobylarz, D.; Moos, W. H.; Bristol, J. A. J. Med. Chem. 1987, 30, 1955-1962 and references therein.
16. (h) Güngör, T.; Fouquet, A.; Teulon, J.-M.; Provost, D.; Gazes, M.; Cloarec, A. J. Med. Chem. 1992, 35, 4455-4463.
17. Carbonic anhydrase inhibitor: (i) Lo, Y. S.; Nolan, J. C.; Maren, T. H.; Welstead, W. J., Jr.; Gripshover, D. F.; Shamblee, D. A. J. Med. Chem. 1992, 35, 4790-4794.
18. AMPA antagonist: (j) Ohmori, J.; Shimizu-Sasamata, M.; Okada, M.; Sakamoto, S. J. Med. Chem. 1996, 39, 3971-3979.
19. COX inhibitor: (k) Almansa, C.; Bartroli, J.; Belloc, J.; Cavalcanti, F. L.; Ferrando, R.; Gomez, L. A.; Ramis, I.; Carceller, E.; Merlos, M.; Garcia-Rafanell, J. J. Med. Chem. 2004, 47, 5579-5582.
20. PDE-4 inhibitor: (l) Jiang, W.; Guan, J.; Macielag, M. J.; Zhang, S.; Qiu, Y.; Kraft, P.; Bhattacharjee, S.; John, T. M.; Haynes-Johnson, D.; Lundeen, S.; Sui, Z. J. Med. Chem. 2005, 48, 2126-2133.
21. Bradykinin B1 antagonist: (m) Su, D.-S.; Markowitz, M. K.; Murphy, K. L.; Wan, B.-L.; Zrada, M. M.; Harrell, C. M.; O'Malley, S. S.; Hess, J. F.; Ransom, R. W.; Chang, R. S.; Wallace, M. A.; Raab, C. E.; Dean, D. C.; Pettibone, D. J.; Freidinger, R. M.; Bock, M. G. Bioorg. Med. Chem. Lett. 2004, 14, 6045-6048.
22. CB-1 antagonist: (n) Lange, J. H. M.; van Stuivenberg, H. H.; Coolen, H. K. A. C.; Adolfs, T. J. P.; McCreary, A. C.; Keizer, H. G.; Wals, H. C.; Veerman, W.; Borst, A. J. M.; de Looff, W.; Verveer, P. C.; Kruse, C. G. J. Med. Chem. 2005, 48, 1823-1838.
23. PDGFR inhibitors: (o) Zhong C.; He, J.; Xue, C.; Li, Y. Bioorg. Med. Chem. 2004, 12, 4009-4015 and references therein.
24. 240 cross-link was found in the active site of cytochrome c oxidase: (a) Yoshikawa, S.; Shinzawa-Itoh, K.; Nakashima, R.; Yaono, R.; Yamashita, E.; Inoue, N.; Yao, M.; Fei, M. J.; Libeu, C. P.; Mizushima, T.; Yamaguchi, H.; Tomizaki, T.; Tsukihara, T. Science 1998, 280, 1723-1729.
25. (b) Bambal, R. B.; Hanzlik, R. P. Chem. Res. Toxicol. 1995, 8, 729-735.
26. For a recent account, see: Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
27. Bambal, R.; Haznlik, R. B. J. Org. Chem. 1994, 59, 729-732. Also, see ref 2a,d,hj.
28. Jacobs, C.; Frotscher, M.; Dannhardt, G.; Hartmann, R. W. J. Med. Chem. 2000, 43, 1841-1851. Also, see ref 2a,b,c,j.
29. (a) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941-2944.
30. (b) Combs, A. P.; Saubern, S.; Rafalski, M.; Lam, P. Y. S. Tetrahedron Lett. 1999, 40, 1623-1626.
31. (c) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418.
32. (d) Collman, J. P.; Zhong, M.; Zhang, C.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.
33. For the use of polymer-supported Cu catalyst, see: (e) Chiang, G. C. H.; Olsson T. Org. Lett. 2004, 6, 3079-3082.
34. 2O or MeOH, see: (a) Collman, J. P.; Zhong M.; Zeng, Li.; Costanzo, S. J. Org. Chem. 2001, 66, 1528-1531.
35. (b) Lan, J.-B.; Chen, L.; Yu, X.-Q.; You, J.-S.; Xie, R. G. Chem. Commun. 2004, 2, 188-189.
36. A "base-free anaerobic" system: Berkel, S. S.; Hoogenband, A.; Terpstra, J. W.; Tromp, M.; Leeuwena, P. W. N. M.; Strijdoncka, G. P. F. Tetrahedron Lett. 2004, 45, 7659-7662.
37. Use of molecular sieves: (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940.
38. (b) References 7a and 11.
39. 2 or in protic solvents (cf. ref 8b).
40. (a) Lopez, A. P.; Avendano, Ć.; Menéndez, J. C. Tetrahedron Lett. 1992, 33, 659-662.
41. (b) J. Org. Chem. 1995, 60, 5678-5682.
42. (c) Elliott, G. I.; Konopelski, J. P. Org. Lett. 2000, 2, 3055-3057.
43. (d) Fedorov, A. U.; Finet, J.-P. Eur. J. Org. Chem. 2004, 9, 2040-2045.
44. Fedorov, A. Y.; Finet, J.-P. Tetrahedron Lett. 1999, 40, 2747-2748.
45. Lam, P. Y. S.; Clark, C. G.; Saunern, S.; Adams, J.; Averill, K.; Chan, D. M. T.; Combs, A. P. Synlett 2000, 674-676.
46. Lam, P. Y. S.; Deudon, S.; Averill, K. M.; Li, R.; He, M. Y.; DeShong, P.; Clark, C. G. J. Am. Chem. Soc. 2000, 122, 7600-7601.
47. Nontransition metal catalyzed direct arylation in ionic liquid: Wang, F.-Y.; Chen, Z.-C.; Zheng, Q.-G. J. Chem. Res. 2004, 206-207.
48. Kiyomori, A.; Marcoux, J.-F.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657-2660.
49. Yue, W.; Lewis, S. I.; Koen, Y. M.; Hanzlik, R. P. Bioorg. Med. Chem. Lett. 2004, 14, 1637-1640.
50. (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727-7729.
51. A later publication suggested that either trans-1,2-cyclohexanediamine or 1,10-phenanthroline was sufficient for aryl iodides: (b) Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578-5587.
52. Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Chem.-Eur. J. 2004, 10, 5607-5622. This report appeared after the completion of our own work. As a result, we have not performed direct comparison with ligand III.
53. Proline-promoted Ullmann coupling: (a) Cai, Q.; Zhu, W.; Zhang, H.; Zhang, Y.; Ma, D. Synthesis 2005, 496-499.
54. (b) Ma, D.; Cai, Q. Synlett 2004, 128-130.
55. A ligandless N-arylation of (S)-1-(3-bromophenyl)-ethylamine under microwave heating (195 °C and 2-3 h): Wu, Y.-J.; He, H.; L'Heureux, A. Tetrahedron Lett. 2003, 44, 4217-4218.
56. See ref 1e and references therein.
57. (a) TEAC is very soluble in most organic solvents and gives nearly homogeneous reaction mixtures. The commercial material from Fluka (90% or 95%) was used in this study.
58. (b) Other soluble bases such as pyridine and TBAF did not yield any products.
59. Based on LC-MS analyses. Some optimizations were carried out under microwave heating at various temperatures.
60. This type of in situ conversion to benzimidazole had been observed before (personal communication with Prof. Stephen L. Buchwald at MIT, 2004).
61. (a) Conversion based on LC-MS analyses. The isolated yield of 1 was 63% from TEAC.
62. (b) These reactions were run in a sealed tube without using any inert gases.
63. 3, and MgO. These experiments were conducted under microwave heating (Smith Synthesizer, from Personal Chemistry, 180 °C, 20 min total) under identical conditions (CuI, IV, DMF).
64. 3 and polymer-supported carbonate were ineffective. (b) TEAC as carboxylating reagents: Arcadi, A.; Inesi, A.; Marinelli, F.; Rossi, L.; Verdecchia, M. Synlett 2005, 67-70 and references therein.
65. (c) TEAC as base for sulfide synthesis: Feroci, M.; Inesi, A.; Rossi, L. Synth. Commun. 1999, 29, 2611-2615.
66. For use of quinolinol ligands in biaryl ether synthesis, see: Pagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A. J. Am. Chem. Soc. 2000, 122, 5043-5051.
67. 3 (Aldrich) as bases, respectively. Both reactions went to completion after 24 h.
68. 2O on the amination reactions has been controversial. For a recent example, see: Meyers, C.; Maes, B. U. W.; Loones, K. T. J.; Bal, G.; Lemière, G. L. F.; Dommisse, R. A. J. Org. Chem. 2004, 69, 6010-6017.
69. A comparison between Scheme 1 and Table 1 offers an example of possible chelation (substrate based) assisted Cu catalysis. We suspect that this was the case in the N-arylation of purine (ref 19b).
70. A small amount of ethylation products (5-10%), likely by TEAC, of benzimidazole or IV, was observed (LC-MS), especially with long reaction times. 8-MeO-quinoline (Trécourt, F.; Mallet, M.; Mongin, F.; Queguiner, G. Synthesis 1995, 1159-1162) as ligand is somewhat less, but still, effective for the reaction.
71. Lower yields were often obtained for polar imidazoloids (see Table 2, entries 3 and 4), partially due to loss of products during workup and purifications.
72. (a) No regioisomers were detected.
73. (b) In the absence of TEAC and ligand (IV), only a trace amount of 18 was formed.
74. 2O were reported to catalyze N-arylation of imidazole with activated chlorides (DMSO, 150 °C): Son, S. U.; Park, I. K.; Park, J.; Hyeon, T. Chem. Commun. 2004, 778-779.
75. (b) Cu(II) apatites were recently reported in the N-arylation of imidazoles with chloroarenes: Choudary, B. C.; Sridhar, C.; Kantam, M. L.; Venkanna, G. T.; Sreedhar, B. J. Am. Chem. Soc. 2005, 127, 9948-9949.