Synthesis 2010(4): 714-717  
DOI: 10.1055/s-0029-1217110
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

A Practical Synthesis of 1-N-SEM-Protected 3-Iodo-7-methyl-2-piperidin-3-ylindole

James G. Phillips*a, Maria Jaworskaa, Willard Lewb
a Curragh Chemistries Inc., c/o Sherwin Williams Cradle, 7650 Hub Parkway, Valley View, OH 44125, USA
e-Mail: [email protected] ;
b Gilead Sciences, 333 Lakeside Drive, Foster City, CA 94404, USA
Further Information

Publication History

Received 31 August 2009
Publication Date:
13 November 2009 (online)

Abstract

A convenient procedure for the preparation of the 1-N-SEM-protected 3-iodo-7-methyl-2-piperidin-3-ylindole 3 is described. This scaffold provides access to unique and diverse 7-methyl-substituted indole libraries.

    References

  • 1 Li JJ. Gribble GW. In Palladium in Heterocyclic Chemistry   Pergamon; London: 2000.  p.73-181  
  • 2a Kocienski PJ. Protecting Groups   3rd ed.:  Thieme Verlag; Stuttgart: 2004. 
  • 2b Greene TW. Wuts PGM. Protecting Groups in Organic Synthesis   3rd ed.:  Wiley-Interscience; New York: 1999.  p.615-631  
  • 3a Illi VO. Synthesis  1979,  136 
  • 3b Conway SC. Gribble GW. Heterocycles  1990,  30:  627 
  • 4 Amat M. Seffar F. Lior N. Bosch J. Synthesis  2001,  267 
  • 5 Lipinska T. Guibe-Jampel E. Petit A. Loupy A. Synth. Commun.  1999,  29:  1349 
  • 6 Augustine RL. Catalytic Hydrogenation   Marcel Dekker; New York: 1965.  p.104-109  
  • 7a Hunsberger IM. Shaw ER. Fugger J. Ketcham R. Lednicer D. J. Org. Chem.  1956,  21:  394 
  • 7b Clasen H. inventors; US Patent 4 066  698.  1978; Chem. Abstr. 1976, 164393
  • 8 Jennings LD. Foreman KW. Rush TS. Tsao DHH. Mosyak L. Kincaid SL. Sukhdeo MN. Sutherland AG. Ding W. Kenny CH. Sabus CL. Liu H. Dushhin EG. Moghazeh SL. Labthavikul P. Peterse PJ. Tuckman M. Ruzin AV. Bioorg. Med. Chem.  2004,  12:  5115 
  • 9 Zhao D. Hughes DL. Bender DR. DeMarco AM. Reider PJ. J. Org. Chem.  1991,  56:  3001 
  • 10 Pfenninger H. A. inventors; US Patent 3 468  894.  1969; Chem. Abstr. 1969, 77795
  • 11 Hutchins SM. Chapman KT. Tetrahedron. Lett.  1996,  37:  4869 
  • 12 Saulnier MG. Gribble GW. J. Org. Chem.  1982,  47:  757