Literature DB >> 25068576

A practical synthesis of indoles via a Pd-catalyzed C-N ring formation.

Rishi G Vaswani1, Brian K Albrecht, James E Audia, Alexandre Côté, Les A Dakin, Martin Duplessis, Victor S Gehling, Jean-Christophe Harmange, Michael C Hewitt, Yves Leblanc, Christopher G Nasveschuk, Alexander M Taylor.   

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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Year:  2014        PMID： 25068576     DOI： 10.1021/ol5018118

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  Gold(I)-Mediated Cycloisomerization/Cycloaddition Enables Bioinspired Syntheses of Neonectrolides B-E and Analogues.

Authors:  Thomas J Purgett; Matthew W Dyer; Bryce Bickel; James McNeely; John A Porco
Journal:  J Am Chem Soc       Date:  2019-09-12       Impact factor: 15.419

2.  l-Serine Biosensor-Controlled Fermentative Production of l-Tryptophan Derivatives by Corynebacterium glutamicum.

Authors:  Lenny Ferrer; Mahmoud Elsaraf; Melanie Mindt; Volker F Wendisch
Journal:  Biology (Basel)       Date:  2022-05-13

3.  Lewis Acid Mediated Vinylogous Additions of Enol Nucleophiles into an α,β-Unsaturated Platinum Carbene.

Authors:  Paul A Allegretti; Khoi Huynh; Tarik J Ozumerzifon; Eric M Ferreira
Journal:  Org Lett       Date:  2015-12-14       Impact factor: 6.005

4.  A New Scalable Synthesis of ELQ-300, ELQ-316, and other Antiparasitic Quinolones.

Authors:  Sovitj Pou; Rozalia A Dodean; Lisa Frueh; Katherine M Liebman; Rory T Gallagher; Haihong Jin; Robert T Jacobs; Aaron Nilsen; David R Stuart; J Stone Doggett; Michael K Riscoe; Rolf W Winter
Journal:  Org Process Res Dev       Date:  2021-08-04       Impact factor: 3.858

5.  An intramolecular C-N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis.

Authors:  Hana Doušová; Radim Horák; Zdeňka Růžičková; Petr Šimůnek
Journal:  Beilstein J Org Chem       Date:  2015-05-27       Impact factor: 2.883

6.  Identification of (R)-N-((4-Methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-1-(1-(1-(2,2,2-trifluoroethyl)piperidin-4-yl)ethyl)-1H-indole-3-carboxamide (CPI-1205), a Potent and Selective Inhibitor of Histone Methyltransferase EZH2, Suitable for Phase I Clinical Trials for B-Cell Lymphomas.

Authors:  Rishi G Vaswani; Victor S Gehling; Les A Dakin; Andrew S Cook; Christopher G Nasveschuk; Martin Duplessis; Priyadarshini Iyer; Srividya Balasubramanian; Feng Zhao; Andrew C Good; Robert Campbell; Christina Lee; Nico Cantone; Richard T Cummings; Emmanuel Normant; Steven F Bellon; Brian K Albrecht; Jean-Christophe Harmange; Patrick Trojer; James E Audia; Ying Zhang; Neil Justin; Shuyang Chen; Jon R Wilson; Steven J Gamblin
Journal:  J Med Chem       Date:  2016-10-28       Impact factor: 7.446
  6 in total

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