Utilization of lithium amide in the synthesis of N-arylanthranilic acids and N-arylanthranilamides

Organic Process Research and Development

Volumn 9, Issue 6, 2005, Pages 843-846

  Davis, Edward M ^a   Nanninga, Thomas N ^a   Tjiong, Howie I ^a   Winkle, Derick D ^a  

^a PFIZER INC   (United States)

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[No Author keywords available]

Indexed keywords

EID: 28944432317     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0501242     Document Type: Article

References (22)

1. (a) Scherrer, R. A.; Short, F. W. U.S. Patent 3,313,848, 1967.
2. (a) Sebolt-Leopold, J. S.; Dudley, D. T.; Herrera, R.; Van Becelaere, K.; Wiland, A.; Gowen, R. C.; Tecle, H.; Barrett, S. D.; Bridges, A.; Przybranowski, S.; Leopold, W. R.; Saltiel, A. R. Nature Medicine; New York, 1999; Vol. 5, pp 810-816.
3. (b) Barrett, S. D.; Bridges, A. J.; Doherty, A. M.; Dudley, D. T.; Saltiel, A. R.; Tecle, H. PCT Int. Appl. WO 199901426.
4. (c) Barrett, S. D.; Kaufman, M. D.; Milbank, J. B.; Rewcastle, G. W.; Spicer, J. A.; Tecle, H. PCT Int. Appl. WO 2003062191.
5. Augelli-Szafran, C. E.; Barvian, M. R.; Bigge, C. F.; Glase, S. A.; Hachiya, S.; Keily, J. S.; Kimura, T.; Lai, Y.; Sakkab, A. T.; Suto, M. J.; Walker, L. C.; Yasunaga, T.; Zhuang, N. PCT Int. Appl. WO 200076489.
6. (a) Bunnett, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273-412.
7. (b) Paine, A. J. J. Am. Chem. Soc. 1987, 109, 1496-1502.
8. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
9. Harris, M. C.; Huang, X.; Buchwald, S. L. Org. Lett. 2002, 4, 2885-2888.
10. Kuwano, R.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2002, 67, 6479-6486.
11. For reviews see: (a) de Meijere, A.; Diederich, F., Eds. Metal Catalyzed Cross-Coupling Reactions, 2nd ed. VCH: 2004.
12. (b) Jiang, L.; Buchwald, S. L. Vol. 2, Chapter 13, pp 699-760 in ref 6a and references therein.
13. (c) Schlummer, B.; Scholz, U. Adv. Synth. Catal. 2004, 346, 1599-1626 and references therein.
14. (a) Sorenson, R. J. J. Org. Chem. 2000, 65, 7747-7749.
15. (b) Combes, S.; Finet, J.-P. Tetrahedron 1998, 4313-4318.
16. Chen, M. H.; Beylin, V. G.; Iakovleva, E.; Kesten, S. J.; Magano, J.; Vrieze, D. Synth. Comm. 2002, 32, 411-417.
17. (b) Chen, M. H.; Magano, J.; U.S. Patent 6,686,499, Feb. 3, 2004.
18. (c) Chen, M. H.; Davis, E. M.; Magano, J.; Nanninga, T. N.; Winkle, D. D. WO 2002018319 A1.
19. (a) Glamkowski, E. J.; Chiang, Y. J. Heterocycl. Chem. 1987, 24, 1599-1604.
20. (b) Kim, D. H. J. Heterocycl. Chem. 1981, 18, 287-291.
21. Hattori, T.; Satoh, S.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 3840-3842.
22. For a related system, see Bahmanyar, S.; Borer, B. C.; Kim, Y. M.; Kurtz, D. M.; Yu, S. Organic Lett. 2005, 7, 1011-1014.