Indole Resin: A Versatile New Support for the Solid-Phase Synthesis of Organic Molecules

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5300-5301

  Estep, Kimberly G ^a   Neipp, Christopher E ^a   Stephens Stramiello, Linda M ^a   Adam, Mavis D ^a   Allen, Martin P ^a   Robinson, Shaughnessy ^a   Roskamp, Eric J ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011667653     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9806052     Document Type: Article

References (20)

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2. (b) Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144-154.
3. (c) Patel, D. V.; Gordon, E. M. Drug Discovery Today 1996, 1, 134-144.
4. (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678.
5. (b) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288-2337.
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7. Boojamra, C. G.; Burow, K. M.; Thompson, L. A.; Ellman, J. J. Org. Chem. 1997, 62, 1240-1256.
8. Holmes, C. P.; Marquess, D. New Linkers for Generating Substituted Amides and Ureas from Solid Supports. Presented at the 213th National Meeting of the American Chemical Society, San Francisco, CA; American Chemical Society: Washington, DC, 1997; ORGN 383.
9. Swayze, E. E. Tetrahedron Lett. 1997, 38, 8465-8468.
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11. Landi, Jr., J. J.; Ramig, K. Synth. Commun. 1991, 21, 167-171.
12. During the preparation of this paper, the synthesis of N-substituted amides using the Rink linker were reported: Garigipati, R. S. Tetrahedron Lett. 1997, 38, 6807-6810. Brown, E. G.; Nuss, J. M. Tetrahedron Lett. 1997, 38, 8457-8460.
13. During the preparation of this paper, the synthesis of N-substituted amides using the Rink linker were reported: Garigipati, R. S. Tetrahedron Lett. 1997, 38, 6807-6810. Brown, E. G.; Nuss, J. M. Tetrahedron Lett. 1997, 38, 8457-8460.
14. Aminomethyl polystyrene resin (1% cross-linked, 200-400 mesh) with a loading of 0.70-0.75 mequiv/g was purchased from Bachem and used without further treatment.
15. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595-598.
16. 3CN can afford impure products in unsatisfactory yield.
17. 2NEt (5 equiv) in DMF.
18. 2 at room temperature was complete in 30 min, as determined by HPLC analysis.
19. The loading of 5 was determined using a "cleave and weigh" procedure: 5 was reductively aminated with p-methoxybenzylamine, acylated with acetic anhydride, and cleaved with 50% TFA/dichloromethane and the resulting acetamide quantified. The loading of 5 was calculated to reflect the amount of acetamide obtained and was typically between 0.5 and 0.7 mequiv/g.
20. Robinson, S.; Roskamp, E. J. Tetrahedron 1997, 53, 6697-6705.