A novel and selective method for the N-arylation of indoles mediated by KF/Al2O3

Tetrahedron Letters

Volumn 37, Issue 3, 1996, Pages 299-302

  Smith III, William J ^a   Sawyer, J Scott ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030070473     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02157-4     Document Type: Article

References (27)

1. th National Organic Symposium, Williamsburg, VA, June 11-15, 1995.
2. Angerer, E.; Strohmeier, J. J. Med. Chem. 1987, 30, 131-136.
3. Glamkowski, E. J.; Fortunato, J. M.; Spaulding, J. F.; Wilker, J. C.; Ellis, D. B. J. Med. Chem. 1985, 28, 66-73.
4. (a) Chapleo, R. B.; Fagan, G. P. Ann. Drug Data Rep. 1993, 15, 59.
5. (b) Chem. Abstr. 1992, 117:90283f.
6. Kamat, A. G.; Gadaginamath, G. S. Indian J. Chem., Sect. B 1994, 33, 255-259.
7. Perregaard, J.; Arnt, J.; Bogeso, K. P.; Hyttel, J.; Sanchez, C. J. Med. Chem. 1992, 35, 1090-1101.
8. (a) Unangst, P. C.; Connor, D. T.; Stabler, S. R.; Weikert, R. J.; Carethers, M. E.; Kennedy, J. A.; Thueson, D. O.; Chestnut, J. C.; Adolphson, R. L.; Conroy, M. C. J. Med. Chem. 1989, 32, 1360-1366.
9. (b) Unangst, P. C.; Carethers, M. E.; Webster, W.; Janik, G. M.; Robichaud, L. J. J. Med. Chem. 1984, 27, 1629-1633.
10. (c) Robichaud, L. J.; Stewart, S. F.; Adolphson, R. L. Int. J. Immunopharmacol. 1987, 9, 41.
11. (d) Wright, C. D.; Hoffman, M. D.; Thueson, D. O. J. Luekocyte Biol. 1987, 42, 30-35.
12. Pozharskii, A. F.; Martsokha, B. K.; Simonov, A. M. J. Gen. Chem. USSR 1963, 33, 994.
13. (a) Barton, D. H. R.; Blazejewski, J. C.; Charpiot, B.; Finet, J. P.; Motherwell, W. B.; Papoula, M. T. B.; Stanforth, S. P. J. Chem. Soc., Perkin Trans. I 1985, 2667-2675.
14. (b) Barton, D. H. R.; Finet, J. P.; Khansi, J.; Tetrahedron Lett. 1988, 29, 1115-1118.
15. Brown, R. A.; Fernando, S. I. S.; Roberts, R. M. G. J. Chem. Soc., Perkin Trans. I 1994, 197-201.
16. (a) Walsh, P. J.; Carney, M. J.; Bergman, R. G. J. Am. Chem. Soc. 1991, 113, 6343-6345.
17. (b) Etkin, N.; Babu, S. D.; Fooks, C. J.; Durst, T. J. Org Chem. 1990, 55, 1093-1096.
18. (c) Vishkakarma, J. N.; Thomas, A.; Apparao, S.; Junjappa, H.; Ila, H. J. Chem. Soc., Perkin Trans. I 1988, 169-173.
19. (d) Yokoyama, M.; Watanabe, S.; Hatanaka, H. Synthesis 1987, 9, 846-848.
20. (e) Schulenberg, J. W. J. Am. Chem. Soc. 1968, 90, 7008.
21. Stabler, R. S.; Jahangir, Syn. Commun. 1994, 24, 123-129.
22. Seki, K.; Ohkura, K. Heterocycles 1994, 37, 993-996.
23. Schmittling, E. A.; Sawyer, J. S. J. Org. Chem. 1993, 58, 3229-3230.
24. Ando, T.; Clark, J. H.; Cork, D. G.; Hanafusa, T.; Ichihara, J.; Kimura, T. Tetrahedron Lett. 1987, 28, 1421-1424.
25. Clark, J. H.; Owen, N. D. S. Tetrahedron Lett. 1987, 28, 3627-3630.
26. Thangaraj, K.; Morgan, L. R. Syn. Commun. 1994, 24, 2063-2067.
27. The 40% potassium fluoride-alumina sold by Aldrich Chemical Co. has not been tested for its catalytic activity in this procedure. For an example of preparing 37% potassium fluoride supported on basic alumina, see: Schmittling, E. A.; Sawyer, J. S. Tetrahedron Lett. 1991, 32, 7207-7210.