title: Solid-phase synthesis of 2,3,5-trisubstituted indoles.
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]
authors.affiliation: Department of Chemistry, Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
authors.forename: T Y
authors.initials: TY
authors.lastname: Wu
authors.forename: S
authors.initials: S
authors.lastname: Ding
authors.forename: N S
authors.initials: NS
authors.lastname: Gray
authors.forename: P G
authors.initials: PG
authors.lastname: Schultz