A practical synthesis of 2-aryl-indole-6-carboxylic acids

Synlett

Volumn , Issue 5, 2004, Pages 883-885

  Gallou, Fabrice ^a   Yee, Nathan ^a   Qiu, Fenghe ^a   Senanayake, Chris ^a   Linz, Guenter ^b   Schnaubelt, Juergen ^b   Soyka, Rainer ^b  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

^b BOEHRINGER INGELHEIM PHARMA GMBH AND CO KG   (Germany)

Author keywords

Indole; Reductive cyclization; SNAr reaction

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; INDOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; COST EFFECTIVENESS ANALYSIS; CYCLIZATION; DECARBOXYLATION; DRUG HYDROLYSIS; DRUG SYNTHESIS; REDUCTION;

EID: 1942521288     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-820015     Document Type: Article

References (22)

1. Kamijo, S.; Yamamoto, Y. J. Org. Chem. 2003, 68, 4764.
2. Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
3. Gribble, G. W. Contemp. Org. Synth. 1994, 1, 145.
4. (a) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251.
5. (b) Rutherford, J. L.; Rainka, M. P.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 15168.
6. (c) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652.
7. (d) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473.
8. Vazquez, E.; Davies, I. W.; Payack, J. F. J. Org. Chem. 2002, 67, 7551; and references therein.
9. (a) Fairley, T. A.; Tidwell, R. R.; Donkor, I.; Naiman, N. A.; Ohemeng, K. A.; Lombardy, R. J.; Bentley, J. A.; Cory, M. J. Med. Chem. 1993, 36, 1746.
10. (b) Izumi, T.; Sugano, M.; Konno, T. J. Heterocycl. Chem. 1992, 29, 899.
11. (c) Clark, C. I.; White, J. M.; Kelly, D. P.; Martin, R. F.; Lobachevsky, P. Aust. J. Chem. 1998, 51, 243.
12. Selvakumar, N.; Reddy, B. Y.; Kumar, G. S.; Iqbal, J. Tetrahedron Lett. 2001, 42, 8395.
13. Quallich, G. J.; Morrissey, P. M. Synthesis 1993, 51.
14. Augustine, R. L.; Gustavsen, A. J.; Wanat, S. F.; Pattison, I. C.; Houghton, K. S.; Koletar, G. J. Org. Chem. 1973, 38, 3004.
15. (a) Loudon, J. D.; Tennant, G. Quart. Rev., Chem. Soc. 1964, 18, 389.
16. (b) Ruhland, B.; Leclerc, G. J. Heterocycl. Chem. 1989, 26, 469.
17. 6): δ = 8.50-7.20 (m, 3 H), 4.09 (s, 2 H), 4.17 (q, 2 H), 1.25 (t, 3 H). Compound 6: MS: calcd 267.24; found: (M + 1) 268.27.
18. NAr reaction was evaluated but showed little improvement. The less expensive and commercially available aryl chloride was preferred in this study.
19. (a) Krapcho, A. P. Synthesis 1982, 805.
20. (b) Gurjar, M.; Reddy, D. S.; Murugaiah, A.; Murugaiah, S. Synthesis 2000, 1659.
21. Challis, B. C.; Rzepa, H. S. J. Chem. Soc., Perkin Trans. 2 1977, 281.
22. Krolski, M. E.; Renaldo, A. F.; Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1988, 53, 1170.