100 gram scale synthesis of a key intermediate of matrix metalloproteinase inhibitor in a continuous-flow system based on a copper-free sonogashira reaction using an ionic liquid as a catalyst support

Takahide Fukuyama*, Md Taifur Rahman, Yukihito Sumino, Ilhyong Ryu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

The key intermediate of matrix metalloproteinase (MMP) inhibitor was synthesized using a flow microreactor for a copper-free Sonogashira coupling reaction in an ionic liquid. The ionic liquid [emim]NTfwas used as a solvent and a catalyst support. A 100 g scale synthesis was achieved in combination with a flow-extraction/catalyst-recycling system, in which the ionic liquid containing the palladium catalyst was continuously recycled.

Original languageEnglish
Pages (from-to)2279-2283
Number of pages5
JournalSynlett
Volume23
Issue number15
DOIs
StatePublished - 20 Aug 2012

Keywords

  • flow reaction
  • ionic liquids
  • matrix metalloproteinase inhibitor
  • microreactor
  • palladium
  • Sonogashira coupling

Fingerprint Dive into the research topics of '100 gram scale synthesis of a key intermediate of matrix metalloproteinase inhibitor in a continuous-flow system based on a copper-free sonogashira reaction using an ionic liquid as a catalyst support'. Together they form a unique fingerprint.

Cite this