title: A practical synthesis of indoles via a Pd-catalyzed C-N ring formation.
abstract: A method for the synthesis of N-functionalized C2-/C3-substituted indoles via Pd-catalyzed C-N bond coupling of halo-aryl enamines is described. The general strategy utilizes a variety of amines and β-keto esters which are elaborated into halo-aryl enamines as latent precursors to indoles. The preferred conditions comprising the RuPhos precatalyst and RuPhos in the presence of NaOMe in 1,4-dioxane tolerate a variety of substituents and are scalable for the construction of indoles in multigram quantities.
authors: Department of Chemistry, Constellation Pharmaceuticals, Inc. , 215 First Street, Suite 200, Cambridge, Massachusetts 02142, United States.
authors: Rishi G
authors: RG
authors: Vaswani
authors: Brian K
authors: BK
authors: Albrecht
authors: James E
authors: JE
authors: Audia
authors: Alexandre
authors: A
authors: Côté
authors: Les A
authors: LA
authors: Dakin
authors: Martin
authors: M
authors: Duplessis
authors: Victor S
authors: VS
authors: Gehling
authors: Jean-Christophe
authors: JC
authors: Harmange
authors: Michael C
authors: MC
authors: Hewitt
authors: Yves
authors: Y
authors: Leblanc
authors: Christopher G
authors: CG
authors: Nasveschuk
authors: Alexander M
authors: AM
authors: Taylor
mesh_terms: D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
chemical_list: D000588:Amines; D007211:Indoles; D010165:Palladium