Synthesis of a 5-substituted benzo[b]thiophene

Heterocycles

Volumn 53, Issue 5, 2000, Pages 1175-1182

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

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIOPHENE DERIVATIVE;

ALKYLATION; ARTICLE; CRYSTALLIZATION; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034192734     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-00-8848     Document Type: Article

References (22)

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3. D. W. Brooks, J. B. Summers, B. P. Gunn, K. E. Rodriques, R. G. Maki, J. F. Dellaria, and J. H. Holms, J. L. Moore; U.S. Patent 4, 992, 464, 1991 (Chem. Abstr., 1991, 115, 135908).
4. a) T. Kolasa and D. W. Brooks, Synthetic Commun., 1993, 23, 743;
5. b) A. Basha, J. D. Ratajczyk, and D. W. Brooks, Tetrahedron Lett., 1991, 32, 3783.
6. Unpublished results.
7. Based on more detailed 2D NMR spectra the impurity was determined to be the 6-substituted dimer. See reference 16.
8. Electrophilic substitution typically occurs at the 3-position on 2-substituted benzo[b]thiophenes: R. M. Scrowton, Adv. Heterocycl. Chem., 1981, 29, 199.
9. a) A. Basha and D. W. Brooks, J. Org. Chem., 1993, 58, 1293;
10. b) H. Kagano, H. Goda, K. Yoshida, and M. Nakano; U.S. Patent 5,298,630, 1994 (Chem. Abstr., 1993, 120, 217260).
11. G. A. Olah, R. Krishnamurti, and G. K. S. Prakash, Comprehensive Organic Synthesis, ed. by B. M. Trost, Peragamon Press, New York, 1984, 3, 310.
12. 1H NMR spectrum of the crude reaction mixture. It was not possible to isolate the minor isomer in a pure form.
13. C. Jutz, Adv. Org. Chem., 1976, 9, pt. 1, 225-342.
14. G. Casiraghi, G. Casnati, G. Puglia, G. Sartori, and G. Terenghi, J. Chem. Soc., Perkin Trans. 1, 1980, 1862.
15. A. Thoer, G. Denis, M. Delmar, and A. Gaset, Synth. Commun., 1988, 18, 2095.
16. H.M. Relles and G. Pizzolato; J. Org. Chem., 1968, 33, 2249.
17. 13C shifts of the methyl groups (G. E. Hawkes, K. Herwig, and J. D. Roberts, J. Org. Chem., 1974, 39, 1017). The anti:syn ratio was 3.2:1 by HPLC.
18. A. R. Haight, G. S. Wayne, G. S. Lannoye, S. I. Parekh, W. Zhang, R.C. Copp, and L.S.Hollis, J. Org. Chem., 1998, 63, 5903.
19. J. D. M. Herscheid and H. C. J. Ottenheijm, Tetrahedron Lett., 1978, 5143.
20. At 72% conversion, the syn/anti ratio was 1/1 by HPLC.
21. E. A. Hill, M. L. Gross, M. Stasiewicz, and M. Manion, 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.