Directed ortho metalation-boronation and Suzuki-Miyaura cross coupling of pyridine derivatives: A one-pot protocol to substituted azabiaryls

Journal of Organic Chemistry

Volumn 72, Issue 5, 2007, Pages 1588-1594

  Alessi, Manlio ^a   Larkin, Andrew L ^b   Ogilvie, Kevin A ^c   Green, Laine A ^d   Lai, Sunny ^a   Lopez, Simon ^e   Snieckus, Victor ^a  

^a QUEEN S UNIVERSITY   (Canada)

^b GLAXOSMITHKLINE   (United States)

^c PFIZER INC   (United States)

^d DALHOUSIE UNIVERSITY   (Canada)

^e UNIVERSIDAD SIMÓN BOLÍVAR   (Venezuela)

Author keywords

[No Author keywords available]

Indexed keywords

DEBORONATION; HETEROCYCLIC SYNTHETIC CHEMISTRY; PYRIDYL BORONATES; PYRIDYL BORONIC ACIDS;

DERIVATIVES; OXIDATION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

PYRIDINE;

AZAFLUORENONE DERIVATIVE; BORONIC ACID DERIVATIVE; CHLOROPYRIDINE DERIVATIVE; FLUORENONE DERIVATIVE; FLUOROPYRIDINE DERIVAIVE; HETEROCYCLIC COMPOUND; O CARBAMOYLPYRIDINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDYLBORONATE DERIVATIVE; PYRIDYLBORONIC ACID DERIVATIVE; PYRIDYLCARBOXAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BORONATION; DIRECTED ORTHO METALATION; ISOMERISM; METAL BINDING; MOLECULAR STABILITY; OXIDATION KINETICS; SUBSTITUTION REACTION; SUZUKI REACTION;

AZA COMPOUNDS; BORON; BORON COMPOUNDS; CHROMATOGRAPHY, THIN LAYER; INDICATORS AND REAGENTS; LITHIUM; MAGNETIC RESONANCE SPECTROSCOPY; METALS; OXIDATION-REDUCTION; PYRIDINES;

EID: 33847659575     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0620359     Document Type: Article

References (115)

1. 2) centers had been one of the most difficult tasks in carbon-carbon bond synthesis until the early 1970s... Now, ... (it) has become the reaction of first choice for thispurpose." Tamao, K. In Comprehensive Organic Synthesis: Trost, B. M., Fleming, I., Ed.: Permagon Press: Oxford, UK, 1991; Vol. 3, p 435.
2. de Meijere, A.; Diederich, F., Eds. Metal-catalyzed Cross Coupling Reactions; Wiley-VCH: Weinheim, Germany, 2004.
3. (a) Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374.
4. (b) Corriu, R.; Masse, J. J. Chem. Soc., Chem. Commun. 1972, 144.
5. (c) Tamao, K. J. Organomet. Chem. 2002, 653, 23.
6. (a) Negishi, E.; King, A.; Okukado, N. J. Org Chem. 1977, 42, 1821-1823.
7. (b) Negishi, E. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York. 2002; pp 229-247.
8. (a) Miyaura, N.; Yamagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513-519.
9. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
10. (c) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633-9695.
11. (a) Milstein, D.; Stille, J. J. Am. Chem. Soc. 1979, 101, 4992-4998.
12. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
13. Rouhi, A. M. Chem. Eng. News 2004, September 6, 49-58.
14. Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 2337-2347, especially p 2345.
15. King, A. O.; Yasuda, N. Top. Organomet. Chem. 2004, 6, 205.
16. (a) Snieckus, V. Chem. Rev. 1990, 90, 879-933.
17. (b) Hartung, C. G.; Snieckus, V. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002: pp 330-367.
18. (c) Macklin, T.; Snieckus, V. In Handbook of C-H Transformations; Dyker, G., Ed.; Wiley: Weinheim, Germany, 2005; pp 106-118.
19. 2), see: Macklin, T.; Snieckus, V. Org. Lett. 2005, 7, 2519-2522.
20. 2) see: Alessi, M.; Zumbansen, K.; Denrchuk, O. M.; Blackburn, T. W.; Snieckus, V. Unpublished results.
21. (a) Anctil, E. J.-G.; Snieckus, V. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 2, pp 761-813.
22. (b) Anctil, E. J.-G.; Snieckus, V. J. Organomet. Chem. 2002, 653, 150-160.
23. (c) Green, L.; Chauder, B.; Snieckus, V. J. Heterocycl. Chem. 1999, 36, 1453-1468.
24. Mitchell, T. N. In Metal-catalyzed Cross Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim. Germany, 2004; pp 125-161.
25. Stanforth, S. P. Tetrahedron 1998, 54, 263-303.
26. Morris, G. A.; Nguyen, S. T. Tetrahedron Lett. 2001, 42, 2093-2096.
27. Benhida, R.; Lecubin, F.; Fourrey, J.-L.; Castellanos, L. R.; Quintero, L. Tetrahedron Lett. 1999, 40, 5701-5703.
28. Liebeskind, L. S.; Wang, J. J. Org. Chem. 1993, 58, 3550-3556.
29. Alvarez, A.; Guzman, A.; Ruiz, A.; Velarde, E. J. Org. Chem. 1992, 57, 1653-1656.
30. Gong, L.-Z.: Knochel, P. Synlett 2005, 267-270.
31. Sakamoto, T.; Kondo, Y.; Murata, N.; Yamanaka, H. Tetrahedron 1993, 49, 9713-9720.
32. Filippini, L.; Gusmeroli, M.; Riva, R., Tetrahedron Lett. 1992, 33, 1755-1758.
33. Minato, A.; Hayashi, K.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1981, 22, 5319-5322.
34. Karig, G.; Thasana, N.; Gallagher, T. Synlett 2002, 808-810
35. Bonnet, V.; Mongin, F.; Trécourt, F.; Breton, G.; Marsais, F.; Knochel, P.; Queginer, G. Synlett 2002, 1008-1010.
36. More recently, pyridines have been cross coupled under Hiyama conditions: (a) Pierrat, P.; Gros, P.; Fort, Y. Org. Lett. 2005, 7, 697-700.
37. (b) Hiyama, T. J. Organomet. Chem. 2002, 653, 58-61.
38. (c) Seganish, W. M.; DeShong, P. J. Org. Chem. 2004, 67, 1137-1143.
39. Tyrrell, E.; Brookes, P. Synthesis 2003, 469-483.
40. Balasubramanian, M.; Keay, J. G. In Comprehensive Heterocyclic Chemistry II: Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, UK, 1996; Vol. 5, pp 245-300.
41. Fischer, F. C.; Havinga, E. Recl. Trav. Chim. Pays-Bas 1974, 93, 21-24.
42. The reaction of 2-pyridyl Grignard with tris(trimethylsilyl)borate has recently been reported to yield the corresponding boronic acid in good yield; Matondo, H.; Souirti, S.; Baboulene, M. Synth. Commun. 2003, 33, 795-800.
43. Ishikura, M.; Mano, T.; Oda, I.; Terashima, M. Heterocycles 1984, 22, 2471-2474.
44. N-Phenyldiethanolamine: (a) Hodgson, P.; Salingue, F. Tetrahedron Lett. 2004, 45, 685-687.
45. Polystyrene-supported diethanolamine: (b) Gros, P.; Doudouh, A.; Fort, Y. Tetrahedron Lett. 2004, 45, 6239-6241.
46. (c) Pfizer Global R & D, Sándwich, Kent, UK, U.S. Patent No. 7,026,479.
47. 3- and 4-pyridineboronic acids (and corresponding esters) are available in milligram to gram quantities from numerous suppliers; e.g., Aldrich Chemical Company, Inc., Milwaukee, WI, USA; Frontier Scientific, Inc., Logan, Utah, USA; CombiPhos Catalysts, Inc., Princeton, NJ, USA; and Lancaster Synthesis, Inc., Windham, NH, USA.
48. (a) Li, W.; Nelson, D. P.; Jensen, M. S.; Hoerrner, R. S.; Dongwei, C.; Larsen, R. D. Org. Lett. 2003, 5, 4835-4837.
49. (b) Reider, P. J. J. Org. Chem. 2002, 67, 5394-5397.
50. Subsequently, 3-pyridylboroxin has been used directly in Suzuki couplings; see: (c) Cioffi, C. L.; Spencer, W. T.; Richards, J. J.; Herr, R. J. J. Org. Chem. 2004, 69, 2210-2212.
51. For examples of large-scale coupling reactions of diethyl(3-pyridyl) borane see: Wei, H.; Sudini, R.; Yin, H. Org. Process Res. Dev. 2004, 8, 955-957.
52. Lipton, M. F.; Mauragis, M. A.; Maloney, M. T.; Veley, M. F.; VanderBor, D. W.; Newby, J. J.; Appell, R. B.; Daugs, E. Org. Process Res. Dev. 2003, 7, 385-392.
53. For the preparation and coupling of 3-pyridyl tetrabutylammonium trifluoroborates, see: (a) Batey, R. A.; Quach, T. D. Tetrahedron Lett. 2001, 42, 9099-9103.
54. For coupling of 3-pyridyl potassium trifluoroborate with 5-bromopyrimidine, see: (b) Molander, G. A.; Biolatto, B. J. Org. Chem. 2003, 68, 4302-4314.
55. For coupling of 3-pyridyl potassium trifluoroborate with aryl chlorides, see: (c) Barder, T. E.; Buchwald, S. L. Org. Lett. 2004, 6, 2649-2652.
56. For lithium-iodine exchange see: Coudret, C. Synth. Commun. 1996, 26, 3543. For lithium-bromine exchange see ref 21b.
57. Takagi, J.; Sato, K.; Hartwig, J. F.; Ishiyama, T.; Miyaura, N. Tetrahedron Lett. 2002, 43, 5649-5651.
58. Mkhalid, I. A. I.; Coventry, D.; Albesa-Jove, D.; Batsanov, A. S.; Howard, J. A. K.; Perutz, R. N.; Marder, T. B. Angew. Chem., Int. Ed. 2006, 45, 489-491.
59. (a) Bouillon, A.; Lancelot, J.-C.; Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron 2002, 58, 2885-2890.
60. (b) Bouillon, A.; Lancelot, J.-C.: Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron 2002, 58, 3323-3328.
61. (c) Bouillon, A.; Lancelot, J.-C.; Bovy, P. R.; Rault, S. Tetrahedron 2002, 58, 4369-4373.
62. (d) Bouillon, A.; Lancelot, J.-C.; Sopkova, J.; de Santos. O.; Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron 2003, 59, 10043-10049.
63. (e) Cailly, T.; Fabis, F.; Bouillon, A.; Lemaître, S.; Sopkova, J.; de Santos, O.; Rault, S. Synlett 2006, 53-56.
64. (a) Parry, P. R.; Bryce, M. R.; Tarbit, B. Synthesis 2003, 7, 1035-1038.
65. (b) Parry, P. R.; Wang, C.; Batsanov, A. S.; Bryce, M. R.; Tarbit, B. J. Org. Chem. 2002, 67, 7541-7543.
66. For cross coupling of these boronic acids see: (c) Thompson, A. E.; Hughes, G.; Batsanov, A. S.; Bryce, M. R.; Parry, P. R.; Tarbit, B. J. Org. Chem. 2005, 70, 388-390.
67. (d) Thompson, A. E.; Batsanov, A. S.; Bryce, M. R.; Saygili, N.; Parry, P. R.; Tarbit, B. Tetrahedron 2005, 61, 5131-5135.
68. (e) Saygili, N.; Batsanov, A. S.; Bryce. M. R. Org. Biomol. Chem. 2004, 2, 852-857.
69. Larkin, A. L. M.Sc. Thesis. Queen's University, Kingston, ON, Canada, 2002.
70. (a) Epsztajn, J.; Berski, Z.; Brzezinski, J.; Jozwiak, A. Tetrahedron Lett. 1980, 21, 4739-4742.
71. (b) Epsztajn, J.; Brzezinski, J.; Jozwiak, A. J. Chem. Res. Synop. 1986, 18-19.
72. Comins, D.; LaMunyon, D. Tetrahedron Lett. 1988, 29, 733-776.
73. Analogous self-condensations are known for ortho-lithiated alkyl benzoates and diethylbenzamides: Upton, C. J.; Beak, P. J. Org. Chem. 1975, 40, 1094-1098.
74. Beak, P.; Brubaker, G. R.; Farney, R. F. J. Am. Chem. Soc. 1976, 98, 3621-3627.
75. Villacampa, M.; Cuesta, E.; Avendaño, C. Tetrahedron 1995, 51, 1259-1264.
76. (a) Krizan, T.; Martin, J. J. Am. Chem. Soc. 1983, 105, 6155-6157.
77. (b) Taylor, S.; Lee, D.; Martin, J. J. Org. Chem. 1983, 48, 4156-4158.
78. (c) Corey, E. J.; Gross, A. W. Tetrahedron Lett. 1984, 25, 495-498.
79. (a) Caron, S.; Hawkins, J. J. Org. Chem., 1998, 63, 2054-2055.
80. 3, see: (b) Kristensen, J.; Lysen, M.; Vedsø, P.; Begtrup, M. Org. Lett. 2001, 3, 1435-1437.
81. For the application of the Caron-Hawkins procedure on N-Boc indole, see: (c) Vazquez, E.; Davies, I. W.; Payack, J. F. J. Org. Chem. 2002, 67, 7551-7552.
82. Recently, a similar one-pot protocol for the hydroxylation of halopyridines has been reported, see: Voisin, A. S.; Bouillon, A.: Lancelot, J.-C.; Rault, S. Tetrahedron 2005, 61, 1417-1421.
83. Green, A. L. M.Sc. Thesis, Queen's University, Kingston, ON, Canada, 2001.
84. Diethanolamine adducts of boronic acids (boroxazolidines), first prepared by Letsinger (Letsinger, R. L.; Skoog, I. J. Am. Chem. Soc. 1955, 77, 2491-2494), have been used for obtaining stable, crystalline derivatives of aryl boronic acids,
85. see: (a) Reference 33.
86. (b) Sharp, M. J.; Cheng, W.; Snieckus, V. Tetrahedron Lett. 1987, 28, 5093-5096.
87. (c) Csuk, R.; Haas, J.; Honig, H.; Weidmann, H. Monatsh. Chem. 1981, 112, 879-882.
88. For procedures for the preparation of pyridyl boronic acid derivatives, see: (d) Pinacol esters, ref 25.
89. (e) Diethanolamine esters, refs 19a, 25d, and: Vedsø, P.; Olesen, P. H.; Hoeg-Jensen, T. Synlett 2004, 892-894.
90. For examples of cross coupling of (a) pinacol pyridylboronates with ArI, ArBr, and ArCl. see: Zhang, J.; Zhao, L.; Song, M.; Mak, T. C. W.; Wu, Y. J. Organomet. Chem. 2006, 691, 1301-1306.
91. Wiles, J. A.; Song, Y.; Wang, Q.; Lucien, E.; Hashimoto, A.; Cheng, J.; Marlor, C. W.; Ou, Y.; Podos, S. D.; Thanassi, J. A.; Thoma, C. L.; Deshpande, M.; Pucci, M. J.; Bradbury, B. J. Bioorg. Med. Chem. Lett. 2006, 16, 1277-1281.
92. Leclerc, N.; Serieys, I.; Attias, A.-J. Tetrahedron Lett. 2003, 44, 5879-5882. ref 25.
93. (b) For pinacol pyridylboronates with inflates see: Coudret, C.; Mazenc. V. Tetrahedron Lett. 1997, 38, 5293-5296.
94. Holzapfel, C. W.; Dwyer, C. Heterocycles 1998, 48, 1513-1518.
95. For DoM chemistry of pyridyl amides, see: Reference 8a. Broussy, S.; Bernardes-Genisson, V.; Gornitzka, H.; Bernadou, J.; Meunier, B. Org. Biomol. Chem. 2005, 3, 666-669.
96. Sammakia, T.; Stangeland, E. L.; Whitcomb, M. C. Org. Lett. 2002, 4, 2385-2388.
97. Guillier, F.; Nivoliers, F.; Godard, A.; Marsais, F.; Queguiner, G.; Siddiqui, M. A.; Snieckus, V. J. Org. Chem. 1995, 60, 292-296.
98. Marsais, M.; Breant, P.; Ginguene, A.; Queguiner, G. J. Organomet. Chem. 1981, 216, 139-147.
99. Gribble, G. W.; Saulnier, M. G. Tetrahedron Lett. 1980, 21, 4137-4140;
100. Heterocycles 1993, 35, 151-169.
101. Review: Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206-2225.
102. For recent cases of use of this Friedel-Crafts anionic equivalency in medicinal and material science synthetic problems, see: Kalinin, A. V.; Reed, M. A.; Norman, B. H.; Snieckus, V. J. Org. Chem. 2003, 68, 5992-5999.
103. McCubbin, J. A.; Tong, X. T.; Wang, R.; Zhao, Y.; Snieckus, V.; Lemieux, R. P. J. Am. Chem. Soc. 2004, 126, 1161-1167.
104. A similar anionic approach to azafluorenones from 2-pyridyl benzoic acid and its derivatives has been reported, see: Tilly, D.; Castanet, A.-S.; Mortier, J. Tetrahedron Lett. 2006, 47, 1121-1123.
105. Rebstock, A.-S.; Mongin, F.; Trécourt, F.; Quéguiner, G. Tetrahedron 2003, 59, 4973-4977.
106. For recent alternative syntheses of fluorenones and azafluorenones, see: Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2006, 45, 3140-3143.
107. Hundsdorf, T.; Neunhoeffer, H. Synthesis 2001, 1800-1805.
108. -1). Experimental details are available in the Supporting Information.
109. Shiao, M.-J.; Peng, C.-J.; Wang, J.-S.; Ma, Y.-T. J. Chin. Chem. Soc. 1992, 39, 173-176.
110. For current biological significance of azabiaryls, see: Chambers, R. J.; Marfat, J. A.; Cheng, J. B.; Cohan, L.; Damon, D. B.; Duplantier, A. G.; Hibbs, T. A.; Jenkinson, T. H.; Johnson, K. L.; Kraus, K. G.; Pettifer, E. R.; Salter, E. D.; Shirley, J. T.; Umland, J. P. Bioorg. Med. Chem. Lett. 1997, 7, 739-744.
111. Zhou, X.-F.; Zhang, L.; Tseng, E.; Scott-Ramsay, E.; Schentag, J. J.; Coburn, R. A.; Morris, M. Drug Metab. Dispos. 2005, 33, 321-328.
112. Smith, R. A.; Hertzog, D. L.; Osterhout, M. H.; Ladouceur, G. H.; Korpusik, M.; Bobko, M. A.; Jones, J. H.; Phelan, K.; Romero, R. H.; Hundertmark, T.; MacDougall, M. L.; Livingston, J. N.; Shoen, W. R. Bioorg. Med. Chem. Lett. 2002, 12, 1303-1306.
113. Denton, T. T.; Zhang, X.; Cashman, J. R. J. Med. Chem. 2005, 48, 224-239. For Mg, Zn, Sn, and Si approaches to azabiaryls, see refs 11, 12, 13, and 14.
114. Stauffer, K. J.; Williams, P. D.; Selnick, H. G.; Nantermet, P. G.; Newton, C. L.; Homnick, C. F.; Zrada, M. M.; Lewis, S. D.; Lucas, B. J.; Krueger, J. A.; Pietrak, B. L.; Lyle, E. A.; Singh, R.; Miller-Stein, C.a; White, R. B.; Wong, B.; Wallace, A. A.; Sitko, G. R.; Cook, J. J.; Holahan, M. A.; Stranieri-Michener, M.; Leonard, Y. M.; Lynch, J. J., Jr.; McMasters, D. R.; Yan, Y. J. Med. Chem. 2005, 48, 2282-2293.
115. Wu, Y.-C; Duh, C.-Y.; Wang, S.-K.; Chen, K.-S.; Yang, T.-H. J. Nat. Prod. 1990, 53, 1327-1331.