Synthesis of alkyl- and aryl-amino-substituted anthraquinone derivatives by microwave-assisted copper(0)-catalyzed Ullmann coupling reactions

Younis Baqi, Christa E. Müller

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

This protocol describes the efficient, generally applicable Ullmann coupling reaction of bromaminic acid with alkyl- or aryl-amines in phosphate buffer under microwave irradiation using elemental copper as a catalyst. the reaction leads to a number of biologically active compounds. As a prototypical example, the synthesis of a new, potent antagonist of human platelet P2Y 12 receptors, which has potential as an antithrombotic drug, is described in detail. The optimized protocol includes a description of an appropriate reaction setup, thin Layer chromatography for monitoring the reaction and a procedure for the isolation, purification and characterization of the anticipated product. The reaction is performed without the use of a glove box and there is no requirement for an inert atmosphere. The reaction typically proceeds within 2-30 min, the protocol, including workup, generally takes 1-3 h to complete.

Original languageEnglish
Pages (from-to)945-953
Number of pages9
JournalNature Protocols
Volume5
Issue number5
DOIs
Publication statusPublished - May 2010

Fingerprint

Anthraquinones
Microwaves
Amines
Copper
Thin layer chromatography
Microwave irradiation
Platelet Aggregation Inhibitors
Thin Layer Chromatography
Platelets
Atmosphere
Purification
Buffers
Phosphates
Catalysts
Monitoring
Pharmaceutical Preparations
bromamine acid

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

Synthesis of alkyl- and aryl-amino-substituted anthraquinone derivatives by microwave-assisted copper(0)-catalyzed Ullmann coupling reactions. / Baqi, Younis; Müller, Christa E.

In: Nature Protocols, Vol. 5, No. 5, 05.2010, p. 945-953.

Research output: Contribution to journalArticle

@article{838aff22d4c14183bde34a894169efc8,
title = "Synthesis of alkyl- and aryl-amino-substituted anthraquinone derivatives by microwave-assisted copper(0)-catalyzed Ullmann coupling reactions",
abstract = "This protocol describes the efficient, generally applicable Ullmann coupling reaction of bromaminic acid with alkyl- or aryl-amines in phosphate buffer under microwave irradiation using elemental copper as a catalyst. the reaction leads to a number of biologically active compounds. As a prototypical example, the synthesis of a new, potent antagonist of human platelet P2Y 12 receptors, which has potential as an antithrombotic drug, is described in detail. The optimized protocol includes a description of an appropriate reaction setup, thin Layer chromatography for monitoring the reaction and a procedure for the isolation, purification and characterization of the anticipated product. The reaction is performed without the use of a glove box and there is no requirement for an inert atmosphere. The reaction typically proceeds within 2-30 min, the protocol, including workup, generally takes 1-3 h to complete.",
author = "Younis Baqi and M{\"u}ller, {Christa E.}",
year = "2010",
month = "5",
doi = "10.1038/nprot.2010.63",
language = "English",
volume = "5",
pages = "945--953",
journal = "Nature Protocols",
issn = "1754-2189",
publisher = "Nature Publishing Group",
number = "5",

}

TY - JOUR

T1 - Synthesis of alkyl- and aryl-amino-substituted anthraquinone derivatives by microwave-assisted copper(0)-catalyzed Ullmann coupling reactions

AU - Baqi, Younis

AU - Müller, Christa E.

PY - 2010/5

Y1 - 2010/5

N2 - This protocol describes the efficient, generally applicable Ullmann coupling reaction of bromaminic acid with alkyl- or aryl-amines in phosphate buffer under microwave irradiation using elemental copper as a catalyst. the reaction leads to a number of biologically active compounds. As a prototypical example, the synthesis of a new, potent antagonist of human platelet P2Y 12 receptors, which has potential as an antithrombotic drug, is described in detail. The optimized protocol includes a description of an appropriate reaction setup, thin Layer chromatography for monitoring the reaction and a procedure for the isolation, purification and characterization of the anticipated product. The reaction is performed without the use of a glove box and there is no requirement for an inert atmosphere. The reaction typically proceeds within 2-30 min, the protocol, including workup, generally takes 1-3 h to complete.

AB - This protocol describes the efficient, generally applicable Ullmann coupling reaction of bromaminic acid with alkyl- or aryl-amines in phosphate buffer under microwave irradiation using elemental copper as a catalyst. the reaction leads to a number of biologically active compounds. As a prototypical example, the synthesis of a new, potent antagonist of human platelet P2Y 12 receptors, which has potential as an antithrombotic drug, is described in detail. The optimized protocol includes a description of an appropriate reaction setup, thin Layer chromatography for monitoring the reaction and a procedure for the isolation, purification and characterization of the anticipated product. The reaction is performed without the use of a glove box and there is no requirement for an inert atmosphere. The reaction typically proceeds within 2-30 min, the protocol, including workup, generally takes 1-3 h to complete.

UR - http://www.scopus.com/inward/record.url?scp=77955482425&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77955482425&partnerID=8YFLogxK

U2 - 10.1038/nprot.2010.63

DO - 10.1038/nprot.2010.63

M3 - Article

VL - 5

SP - 945

EP - 953

JO - Nature Protocols

JF - Nature Protocols

SN - 1754-2189

IS - 5

ER -