An S(N)Ar-based preparation of 1-(2-, 3-, and 4-pyridyl)indoles using potassium fluoride/alumina

Heterocycles

Volumn 51, Issue 1, 1999, Pages 157-160

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

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 PYRIDYL)INDOLE; 1 (3 PYRIDYL)INDOLE; 1 (4 PYRIDYL)INDOLE; ALUMINUM OXIDE; DIMETHYL SULFOXIDE; INDOLE DERIVATIVE; POTASSIUM FLUORIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032874327     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-98-8344     Document Type: Article

References (13)

1. This work was previously presented at the 34th National Organic Symposium, Williamsburg, VA, June 11-15, 1995.
2. W. J. Smith III and J. S. Sawyer, Tetrahedron Lett., 1996, 37, 299.
3. J. S. Sawyer, E. A. Schmittling, J. A. Palkowitz, and W. J. Smith III, J. Org. Chem., 1998, 63, 6338.
4. C. B. Chapleo and G. P. Pagan, Drug Data Rep., 1993, 15, 59.
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7. M. A. Khan and J. B. Polya, J. Chem. Soc. C, 1970, 85;
8. 2 antagonists, see: K. Andersen, J. Perregaard, J. Arnt, J. B. Nielsen, and M. Begtrup, J. Med. Chem., 1992, 35, 4823
9. K. Ohkura, K. Seki, M. Terashima, and Y. Kanaoka, Heterocycles, 1990, 31, 1833, and references cited therein.
10. K. Seki, K. Ohkura, M. Terashima, and Y. Kanaoka, Heterocycles, 1994, 37, 993.
11. F. Maassarani, M. Pfeffer, J. Spencer, and E. Wehman, J. Organomet. Chem., 1994, 466, 265.
12. For an example of this strategy, see: R. S. Stabler and Jahangir, Syn. Commun., 1994, 24, 123.
13. The 40% potassium fluoride-alumina sold by Aldrich Chemical Co. has not been tested for activity in this procedure. For the preparation of 37% potassium fluoride supported on alumina, see: E. A. Schmittling and J. S. Sawyer, Tetrahedron Lett., 1991, 32, 7207.