Solid phase synthesis of spiroindoline

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1497-1500

  Cheng, Yuan ^a   Chapman, Kevin T ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031550841     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00139-1     Document Type: Article

References (10)

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2. (b) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
3. (c) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600, and references therein.
4. 2. Patchett, A. A.; Nargund, R. P.; Tata, J. R.; Chen, M.-H.; Barakat, K. J.; Johnston, D. B. R.; Cheng, K.; Chan, E. W.-S.; Butler, B.; Hickey, G.; Jacks, T.; Schleim, K.; Pong, S.-S.; Chaung, L.-Y. P.; Chen, H. Y.; Frazier, E.; Leung, K. H.; Chiu, S.-H. L.; Smith, R. G. Proc. Natl. Acad. Sci. USA 1994, 92, 7001.
5. 3. (a) Robinson, B. The Fischer Indole Synthesis; John Wiley & Sons: New York, 1982.
6. (b) Robinson, B. Chem. Rev. 1969, 69, 227.
7. 4. Maligres, P. E.; Houpis, I.; Rossen, K.; Molina, A.; Sager, J.; Upadhyay, V.; Wells, K. M.; Reamer, R. A.; Lynch, J. E.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron 1997, in press.
8. 3N at 50 °C overnight. The resin was removed by filtration and the sample was concentrated to dryness.
9. 6. Analysis by HPLC using a 4 × 100 mm Zorbax SB-C8 column (5μ particle size) with a gradient of 10% acetonitrile/water containing 0.1 % TFA to 100% acetonitrile over 10 min. Peak areas were integrated at 220 nm.
10. 7. Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 32, 7571.