Literature DB >> 20860393

Palladium-catalyzed amination of unprotected halo-7-azaindoles.

Jaclyn L Henderson1, Sarah M McDermott, Stephen L Buchwald.   

Abstract

Simple and efficient procedures for the Pd-catalyzed cross-coupling of primary and secondary amines with halo-7-azaindoles(pyrrolo[2,3-b]pyridine) are presented. Previously, no general method was available to ensure the highly selective reaction of the heteroaryl halide in the presence of the unprotected azaindole N-H. Using palladium precatalysts recently reported by our group, such reactions are easily accomplished under mild conditions that can be applied to cross-coupling reactions with a wide array of aliphatic and aromatic amines.

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Year:  2010        PMID: 20860393      PMCID: PMC3142919          DOI: 10.1021/ol101928m

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


  13 in total

1.  Efficient pd-catalyzed amination of heteroaryl halides.

Authors:  Mark D Charles; Phillip Schultz; Stephen L Buchwald
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

2.  Evidence for the formation and structure of palladacycles during Pd-catalyzed C-N bond formation with catalysts derived from bulky monophosphinobiaryl ligands.

Authors:  Eric R Strieter; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-30       Impact factor: 15.336

Review 3.  Analysis of the reactions used for the preparation of drug candidate molecules.

Authors:  John S Carey; David Laffan; Colin Thomson; Mike T Williams
Journal:  Org Biomol Chem       Date:  2006-05-03       Impact factor: 3.876

4.  The copper-catalyzed N-arylation of indoles.

Authors:  Jon C Antilla; Artis Klapars; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2002-10-02       Impact factor: 15.419

5.  Electronic effects on the selectivity of pd-catalyzed C-N bond-forming reactions using biarylphosphine ligands: the competitive roles of amine binding and acidity.

Authors:  Mark R Biscoe; Timothy E Barder; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  3-((4-(4-Chlorophenyl)piperazin-1-yl)-methyl)-1H-pyrrolo-2,3-b-pyridine: an antagonist with high affinity and selectivity for the human dopamine D4 receptor.

Authors:  J J Kulagowski; H B Broughton; N R Curtis; I M Mawer; M P Ridgill; R Baker; F Emms; S B Freedman; R Marwood; S Patel; S Patel; C I Ragan; P D Leeson
Journal:  J Med Chem       Date:  1996-05-10       Impact factor: 7.446

7.  Efficient palladium-catalyzed N-arylation of indoles.

Authors:  D W Old; M C Harris; S L Buchwald
Journal:  Org Lett       Date:  2000-05-18       Impact factor: 6.005

8.  Synthesis and biological evaluation of 7-azaindole derivatives, synthetic cytokinin analogues.

Authors:  Jérome Guillard; Maÿlis Decrop; Nathalie Gallay; Claire Espanel; Elodie Boissier; Olivier Herault; Marie-Claude Viaud-Massuard
Journal:  Bioorg Med Chem Lett       Date:  2007-01-19       Impact factor: 2.823

9.  Concise and efficient synthesis of 4-fluoro-1H-pyrrolo[2,3-b]pyridine.

Authors:  Carl Thibault; Alexandre L'Heureux; Rajeev S Bhide; Réjean Ruel
Journal:  Org Lett       Date:  2003-12-25       Impact factor: 6.005

10.  Impact of donor-acceptor geometry and metal chelation on photophysical properties and applications of triarylboranes.

Authors:  Zachary M Hudson; Suning Wang
Journal:  Acc Chem Res       Date:  2009-10-20       Impact factor: 22.384

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  8 in total

1.  Efficient Pd-catalyzed amination reactions for heterocycle functionalization.

Authors:  Jaclyn L Henderson; Stephen L Buchwald
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

2.  Development of Kinase-Selective, Harmine-Based DYRK1A Inhibitors that Induce Pancreatic Human β-Cell Proliferation.

Authors:  Kunal Kumar; Peng Wang; Roberto Sanchez; Ethan A Swartz; Andrew F Stewart; Robert J DeVita
Journal:  J Med Chem       Date:  2018-08-21       Impact factor: 7.446

3.  Palladium-catalyzed C,N-cross coupling reactions of 3-halo-2-aminopyridines.

Authors:  Felix Perez; Ana Minatti
Journal:  Org Lett       Date:  2011-03-25       Impact factor: 6.005

4.  An Improved Synthesis of BrettPhos and RockPhos-Type Biarylphosphine Ligands.

Authors:  Naoyuki Hoshiya; Stephen L Buchwald
Journal:  Adv Synth Catal       Date:  2012-06-27       Impact factor: 5.837

Review 5.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

6.  Biaryl Monophosphine Ligands in Palladium-Catalyzed C-N Coupling: An Updated User's Guide.

Authors:  Bryan T Ingoglia; Corin C Wagen; Stephen L Buchwald
Journal:  Tetrahedron       Date:  2019-05-11       Impact factor: 2.457

7.  Palladium-catalyzed amination of unprotected five-membered heterocyclic bromides.

Authors:  Mingjuan Su; Naoyuki Hoshiya; Stephen L Buchwald
Journal:  Org Lett       Date:  2014-01-13       Impact factor: 6.005

8.  Palladium-catalyzed C-N and C-O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols.

Authors:  Rajendra Surasani; Dipak Kalita; A V Dhanunjaya Rao; K B Chandrasekhar
Journal:  Beilstein J Org Chem       Date:  2012-11-19       Impact factor: 2.883

  8 in total

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