Characterization and Synthesis of a 6-Substituted Benzo[b]thiophene

Journal of Organic Chemistry

Volumn 63, Issue 17, 1998, Pages 5903-5907

  Haight, Anthony R ^a   Wayne, Gregory S ^a   Lannoye, Gregory S ^a   Parekh, Shyamal I ^a   Zhang, Weijiang ^a   Copp, Richard R ^a   Hollis, L Steven ^b  

^a Chemical Process Research   (United States)

^b ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001120492     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980537j     Document Type: Article

References (22)

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2. Brooks, D. W.; Carter, G. W. In The Search for Antiinflammatory Drugs; Merluzzi, V. J., Adams, J., Eds.; Burkhauser: Boston, 1995; Chapter 5.
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4. (a) Kolasa, T.; Brooks, D. W. Synth. Commun. 1993, 23, 743.
5. (b) Basha, A.; Ratajczyk, J. D.; Brooks, D. W. Tetrahedron Lett. 1991, 32, 3783.
6. Electrophilic substitution typically occurs at the 3-position on 2-substituted benzo[b]thiophenes: Scrowton, R. M. Adv. Heterocycl. Chem. 1981, 29, 199.
7. (a) Basha, A.; Brooks, D. W. J. Org. Chem. 1993, 58, 1293.
8. (b) Kagano, H.; Goda, H.; Yoshida, K.; Nakano, M. U.S. Pat. 5,298,630, 1994.
9. Olah, G. A.; Krishnamurti, R.; Prakash, G. K. S. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1984; Vol. 3, p 310.
10. Ratios were determined by HPLC.
11. Votterro, C., Labat, Y., Poisier, J. M., U.S. Pat. 5113019, 1992.
12. Stokker, G. E., Deana, A. A., deSolms, S. J., Schultz, E. M., Smith, R. L., Cragoe, E. J., Baer, J. E., Ludden, C. T., Russo, H. F., Scriabine, A., Sweet, C. S., Watson, L. S. J. Med. Chem. 1980, 23, 1414.
13. Farah, B. S., Gilbert, E. E. J. Org. Chem. 1963, 28, 2807.
14. Assignment of the regiochemistry of 9 and 10 was additionally based on comparison of an authentic sample of 14 to an authentic sample of the 5′-regioisomer of 14 prepared independently (A. R. Haight, G. S. Wayne, G. S. Lannoye, W. Zhang, unpublished results).
15. Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1986, 27, 3931.
16. Mancuso, A. J.; Brownfair, D. S.; Swern, D. J. Org. Chem. 1979, 44, 4148.
17. 13C shifts of the methyl groups (Hawkes, G. E.; Herwig, K.; Roberts, J. D. J. Org. Chem. 1974, 39, 1017).
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19. We are unaware of any examples where the rate of reduction of an oxime is dependent upon the stereochemistry of the oxime.
20. At 72% conversion, the syn/anti ratio was 2/1 by HPLC.
21. Hill, E. A.; Gross, M. L.; Stasiewicz, M.; Manion, M. J. Am. Chem. Soc. 1969, 91, 7381.
22. 1H NMR spectrum of the crude reaction mixture. It was not possible to isolate the minor isomer in a pure form.