A practical synthesis of indoles via a Pd-catalyzed C-N ring formation
Rishi G Vaswani1, Brian K Albrecht, James E Audia
1Department of Chemistry, Constellation Pharmaceuticals, Inc. , 215 First Street, Suite 200, Cambridge, Massachusetts 02142, United States.
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.
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