Cu-catalyzed N-arylation of oxazolidinones: An efficient synthesis of the κ-opioid receptor agonist CJ-15161

Journal of Organic Chemistry

Volumn 71, Issue 3, 2006, Pages 1258-1261

  Ghosh, Arun ^a   Sieser, Janice E ^a   Caron, Stéphane ^a   Couturier, Michel ^a   Dupont Gaudet, Kristina ^a   Girardin, Melina ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINO ACIDS; CATALYSIS; COPPER; MOLECULAR STRUCTURE;

1,2-AMINO ALCOHOLS; N-ARYLATION; OXAZOLIDINONES;

KETONES;

AMINOALCOHOL; CARBAMIC ACID; CJ 15161; COPPER; EPOXIDE; KAPPA OPIATE RECEPTOR AGONIST; LIGAND; OXAZOLIDINEDIONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CROSS COUPLING REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH TEMPERATURE; NEGISHI REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; RING OPENING; STILLE REACTION; STOICHIOMETRY; SUZUKI REACTION;

AMINATION; BROMIDES; CATALYSIS; COPPER; MOLECULAR STRUCTURE; OXAZOLIDINONES; PYRROLIDINES; RECEPTORS, OPIOID, KAPPA;

EID: 32144461710     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052060z     Document Type: Article

References (30)

1. (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
2. (b) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580.
3. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
4. (d) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144-1157.
5. (e) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158- 1174 and references therein.
6. (a) Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 21, 7525-7546.
7. (b) Yang, B. H.; Buchwald, S. L. Org. Lett. 1999, 1, 35-37.
8. (c) Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101-1104.
9. (d) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043-6048.
10. (a) For a related process, see: Wang, Z.; Skerlj, R. T.; Bridger, G. J. Tetrahedron Lett. 1999, 40, 3543-3546.
11. (b) Arterburn, J. B.; Rao, K. V.; Ramdas, R.; Dible, B. R. Org. Lett. 2001, 3, 1351-1354.
12. (c) Shakespeare, W. C. Tetrahedron Lett. 1999, 40, 2035-2038.
13. For intramolecular amidation, see: Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525-7546.
14. Recently, improvements including use of truly catalytic copper salt as well as significantly milder conditions have been described: (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727-7729. The effect of various diamine ligands on the efficiency of the aryl amidation reaction have been reported:
15. (b) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428. For the first report on intramolecular amidations under relatively mild conditions, see:
16. (c) Kametani, T.; Ohsawa, T.; Ihara, M. Heterocycles 1980, 14, 277-280. For reviews on Cu-catalyzed cross-coupling reactions, see:
17. (d) Lindley, J. Tetrahedron 1984, 40, 1435-1456.
18. (d) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
19. For a recent review on therapeutic oxazolidinones, see: (a) Halle, E.; Majcher-Peszynska, J.; Drewelow, B. Chemother. Journal 2002, 11, 1 -11. For some related work in this area, see:
20. (b) Tucker, J. A.; Allwine, D. A.; Grega, K. C.; Barbachyn, M. R.; Klock, J. L.; Adamski, J. L.; Brickener, S. J.; Hutchinson, D. K.; Ford, C. W.; Zurenko, G. E.; Conradi, R. A.; Burton, P. S.; Jensen, R. M. J. Med. Chem. 1998, 41, 3727-3735.
21. (c) Genin, M. J.; Hutchinson, D. K.; Allwine, D. A.; Hester, J. B.; Hemmert, D. E.; Garmon, S. A.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H.; Friis, J. M.; Shobe, E. M.; Adams, W. J. J. Med. Chem. 1998, 41, 5144-5147.
22. (d) Cleave, D. M.; Brickner, S. J.; Manninen, P. R.; Allwine, D. A.; Lovasz, K. D.; Rohrer, D. C.; Tucker, J. A.; Zurenko, G. E.; Ford, C. W. Bioorg. Med. Chem. Lett. 1998, 8, 1231-1236.
23. (e) Cleave, D. M.; Brickner, S. J. J. Org. Chem. 1996, 61, 6470-6474.
24. (a) Ghosh, A.; Sieser, J. E.; Riou, M.; Cai, W.; Rivera-Ruiz, L. Org. Lett. 2003, 5, 2207-2210. For other reports on cross-coupling of aryl halide with oxaziolidinone under Pd- or Cu-catalyzed conditions, see:
25. (b) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541.
26. (c) Madar, D. J.; Kopecka, H.; Pireh, D.; Pease, J.; Pliushchev, M.; Sciotti, R. J.; Wiedman, P. E.; Djuric, S. W. Tetrahedron Lett. 2001, 42, 3681-3684.
27. (d) Mallesham, B.; Rajesh, B. M.; Rajmohan Reddy, P.; Srinivas, D.; Trehan, S. Org. Lett. 2003, 5, 963-965.
28. (e) Caron, S.; Ghosh, A.; Sieser, J. E. WO 2004039788 A1, 2004.
29. (a) Couturier, M.; Tucker, J. L.; Andresen, B. M.; DeVries, K. M.; Vanderplas, B. C.; Ito, F. Tetrahedron: Asymmetry 2003, 22, 3517-3523.
30. (b) Gehosh, A.; Sieser, J. E.; Caron, S.; Watson, T. J. N. Chem. Commun. (Cambridge) 2002, 15, 1644-1645.