Palladium-catalyzed direct arylation of imidazolone N-oxides with aryl bromides and its application in the synthesis of GSK2137305

Organic Letters

Volumn 14, Issue 7, 2012, Pages 1872-1875

  Zhao, He ^a   Wang, Ruifang ^a   Chen, Ping ^a   Gregg, Brian T ^a   Hsia, Ming Min ^a   Zhang, Wei ^a  

^a ALBANY MOLECULAR RESEARCH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINATED HYDROCARBON; GSK2137305; IMIDAZOLE DERIVATIVE; IMIDAZOLONE; PALLADIUM; SPIRO COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROCARBONS, BROMINATED; IMIDAZOLES; MOLECULAR STRUCTURE; PALLADIUM; SPIRO COMPOUNDS;

EID: 84859577906     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300468g     Document Type: Article

References (56)

1. Appleton, D. R.; Page, M. J.; Lambert, G.; Berridge, M. V.; Copp, B. R. J. Org. Chem. 2002, 67, 5402
2. Graham, J. P.; Langlade, N.; Northall, J. M.; Roberts, A. J.; Whitehead, A. J. Org. Process Res. Dev. 2011, 15, 44
3. Ueda, S.; Su, M.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 700
4. Blunt, R.; Cooper, D. G.; Porter, R. A. WO 2009034061, 2009.
5. Ahmad, N. M.; Lai, J. Y. Q.; Andreotti, D. WO 2008092876, 2008.
6. Coulton, S.; Porter, R. A. WO 2008092872, 2008
7. Demong, D. E.; Miller, M. W.; Dai, X.; Wong, M. K.; Lavey, B. J.; Yu, W.; Zhou, G.; Stamford, A. W.; Kozlowski, J. A.; Greenlee, W. J.; Zhao, H.; Chen, P.; Lin, P.; Dai, P.; Davis, J. L. WO 2011119541, 2011.
8. Stamford, A.; Miller, M. W.; Demong, D. E.; Greenlee, W. J.; Kozlowski, J. A.; Lavey, B. J.; Wong, M. K. C.; Yu, W.; Dai, X.; Yang, D.-Y.; Zhou, G. WO 2010039789, 2010.
9. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
10. Han, W.; Ofial, A. R. Synlett 2011, 1951.
11. Hirano, K.; Miura, M. Synlett 2011, 294
12. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
13. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
14. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677
15. Chen, X.; Engle, K.-M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
16. Ackermann, L. Pure Appl. Chem. 2009, 82, 1403
17. Lewis, J. C.; Bergman, R. C.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013
18. Li, B.-J.; Yang, S.-D.; Shi, Z.-J. Synlett 2008, 949
19. Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rew. 2007, 36, 1173
20. Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200
21. Campeau, L.-C.; Rousseaux, S.; Fagnou, K. J. Am. Chem. Soc. 2005, 127, 18020
22. Bellina, F.; Rossi, R. Tetrahedron 2009, 65, 10269
23. Ackermann, L.; Vicente, R.; Kapai, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
24. McGlacken, G. P.; Bateman, L. M. Chem. Soc. Rev. 2009, 38, 2447
25. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
26. Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Aldrichimica Acta 2007, 40, 35
27. Duric, S.; Tzschucke, C. C. Org. Lett. 2011, 13, 2310
28. Ackermann, L.; Fenner, S. Chem. Commun. 2011, 47, 430
29. Sun, H.-Y.; Gorelsky, S. I.; Stuart, D. R.; Campeau, L.-C.; Fagnou, K. J. Org. Chem. 2010, 75, 8180
30. Schipper, D. J.; Mohamed, E.-S.; Whipp, C. J.; Fagnou, K. Tetrahedron 2009, 65, 4977
31. Schipper, D. J.; Campeau, L.-C.; Fagnou, K. Tetrahedron 2009, 65, 3155
32. Huestis, M. P.; Fagnou, K. Org. Lett. 2009, 11, 1357
33. Campeau, L.-C.; Stuart, D. R.; Leclerc, J.-P.; Megan, B.-L.; Villemure, E.; Sun, H.-Y.; Lasserre, S.; Guimond, N.; Lecavallier, M.; Fagnou, K. J. Am. Chem. Soc. 2009, 131, 3291
34. Campeau, L.-C.; Megan, B.-L.; Leclerc, J.-P.; Villemure, E.; Gorelsky, S.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3276
35. Campeau, L.-C.; Schipper, D. J.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3266
36. Leclerc, J.-P.; Fagnou, K. Angew. Chem., Int. Ed. 2006, 45, 7781
37. Bliss, B. I.; Ahmed, F.; Iyer, S.; Lin, W.; Walker, J.; Zhao, H. Tetrahedron Lett. 2010, 51, 3259
38. Cheng, S.; Wu, H.; Hu, X. Synth. Commun. 2007, 37, 297
39. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley & Sons: New York, 1999; pp 639-640.
40. Compound 3c was prepared according to a similar procedure reported in the reference: Dai, X.; Miller, M. W.; Stamford, A. W. Org. Lett. 2010, 12, 2718. See Supporting Information for detailed experimental
41. Kokatla, H. P.; Thomson, P. F.; Bae, S.; Doddi, V. R.; Lakshman, M. K. J. Org. Chem. 2011, 76, 7842
42. Mikami, Y.; Noujima, A.; Mitsudome, T.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Chem.-Eur. J. 2011, 17, 1768
43. Gowda, N. B.; Rao, G. K.; Ramakrishna, R. A. Tetrahedron Lett. 2009, 51, 5690
44. Caliskan, H.; Zaim, O. Synth. Commun. 2010, 40, 3078
45. Reis, P. M.; Royo, B. Tetrahedron Lett. 2009, 50, 949
46. Fuentes, J. A.; Clarke, M. L. Synlett 2008, 2579
47. Ponaras, A. A.; Zaim, O. J. Heterocycl. Chem. 2007, 44, 487
48. Saini, A.; Kumar, S.; Sandhu, J. S. Synlett 2006, 395
49. Balicki, R. Synthesis 1989, 645
50. Aoyagi, Y.; Abe, T.; Ohta, A. Synthesis 1997, 891
51. Julemont, F.; deLeval, X.; Michaux, C.; Renard, J.-F.; Winum, J.-Y.; Montero, J.-L.; Damas, J.; Dogne, J.-M.; Pirotte, B. J. Med. Chem. 2004, 47, 6749
52. Cividino, P.; Dheu-Andries, M.-L.; Ou, J.; Milet, A.; Py, S.; Toy, P. H. Tetrahedron Lett. 2009, 51, 7038
53. Kanyiva, K. S.; Nakao, Y.; Hiyama, T. Angew. Chem., Int. Ed. 2007, 46, 8872
54. Familoni, O. B.; Klaas, P. J.; Lobb, K. A.; Pakade, V. E.; Kaye, P. T. Org. Biomol. Chem. 2006, 4, 3960
55. Bremner, D. H.; Dunn, A. D.; Wilson, K. A.; Sturrock, K. R.; Wishart, G. Synthesis 1997, 949
56. Bruton, G.; Cooper, I. R.; Orlek, B. S. WO 2006040192, 2006