Organic Letters 2001-11-29

Solid-phase synthesis of 2,3,5-trisubstituted indoles.

T Y Wu, S Ding, N S Gray, P G Schultz

Index: Org. Lett. 3 , 3827-3830, (2001)

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Abstract

2,3,5-Trisubstituted indoles are synthesized in three steps starting from resin-bound aniline 2. R1 is introduced by a palladium-mediated coupling of the aryl iodide with terminal alkynes followed by intramolecular cyclization to form the indole core. Acylation at C-3 with an acid chloride in the presence of AlCl(3) catalyst introduces R2. The indole C-5 position is then diversified either by Sonagashira or Suzuki couplings with the aryl bromide. Finally, indole N-1 can be modified by post-cleavage methylation. [reaction: see text]