Synthesis 2014; 46(23): 3263-3267
DOI: 10.1055/s-0034-1378554
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 4-Halogenated 3-Fluoro-6-methoxyquinolines: Key Building Blocks for the Synthesis of Antibiotics

Thomas Flagstad
a   Department of Chemistry, Technical University of Denmark, 2800 Kgs. Lyngby, Denmark   Fax: + 45(4593)3968   eMail: ten@kemi.dtu.dk
,
Mette T. Petersen
a   Department of Chemistry, Technical University of Denmark, 2800 Kgs. Lyngby, Denmark   Fax: + 45(4593)3968   eMail: ten@kemi.dtu.dk
,
Daniel M. Hinnerfeldt
a   Department of Chemistry, Technical University of Denmark, 2800 Kgs. Lyngby, Denmark   Fax: + 45(4593)3968   eMail: ten@kemi.dtu.dk
,
Michael Givskov
b   Department of International Health, Immunology and Microbiology, Faculty of Health and Medical Sciences, University of Copenhagen, 2200 Copenhagen, Denmark
c   Singapore Centre on Environmental Life Sciences Engineering, Nanyang Technological University, Singapore 637551, Singapore
,
Thomas E. Nielsen*
a   Department of Chemistry, Technical University of Denmark, 2800 Kgs. Lyngby, Denmark   Fax: + 45(4593)3968   eMail: ten@kemi.dtu.dk
c   Singapore Centre on Environmental Life Sciences Engineering, Nanyang Technological University, Singapore 637551, Singapore
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Publikationsverlauf

Received: 11. Juni 2014

Accepted after revision: 07. Juli 2014

Publikationsdatum:
28. August 2014 (online)


Abstract

A practical and scalable 4-step route is presented for the synthesis of 4-bromo-3-fluoro-6-methoxyoquinoline and 3-fluoro-4-iodo-6-methoxyoquinoline from readily available 2,4-dichloro-3-fluoroquinoline with an overall yield of 81–85%. Halogenated quinoline building blocks have found much use in antimicrobial drug discovery, and the method reported here would be useful for the synthesis of these compounds.

Supporting Information

 
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