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

Thomas Flagstad, Mette Terp Petersen, Daniel Michael Hinnerfeldt, Michael Christian Givskov, Thomas Eiland Nielsen

Research output: Contribution to journalJournal articleResearchpeer-review

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. © Georg Thieme Verlag.
Original languageEnglish
JournalSynthesis
Volume46
Issue number26
Pages (from-to)3263–3267
ISSN0039-7881
DOIs
Publication statusPublished - 2014

Keywords

  • Catalysis
  • Organic Chemistry
  • antibiotic
  • fluorine
  • heterocycle
  • quinolone
  • regioselectivity

Cite this

Flagstad, T., Petersen, M. T., Hinnerfeldt, D. M., Givskov, M. C., & Nielsen, T. E. (2014). Synthesis of 4-Halogenated 3-Fluoro-6-methoxyquinolines: Key Building Blocks for the Synthesis of Antibiotics. Synthesis, 46(26), 3263–3267. https://doi.org/10.1055/s-0034-1378554