Synthesis of a Pinacol Boronate Precursor for [18F]Rucaparib Radiosynthesis

Ju Ahn Seo, Jinjae Park, Cheol Hong Cheon

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

A novel synthetic approach toward pinacol boronate used as a precursor in the recent radiosynthesis of [18F]rucaparib is described in this study. The Heck reaction of an ortho-iodoaniline derivative bearing a chloride group at the meta-position with acrylonitrile produced the desired (E)-2-aminocinnamonitrile derivative. The subsequent cyanide-catalyzed imino-Stetter reaction of aldimine derived from the obtained 2-aminocinnamonitrile and aldehyde afforded the required trisubstituted indole-3-acetonitrile. The reduction of the nitrile group with cobalt boride followed by the construction of an azepinone scaffold generated indoloazepinone bearing a chloride substituent at the C6-position of the indole scaffold. The Suzuki–Miyaura borylation of the chloride substituent produced pinacol boronate previously used in the synthesis of [18F]rucaparib. Detailed outcomes of different approaches using different 2-aminocinnamonitriles were discussed as well.

Original languageEnglish
Article numbere202300501
JournalAsian Journal of Organic Chemistry
Volume13
Issue number1
DOIs
Publication statusPublished - 2024 Jan

Bibliographical note

Publisher Copyright:
© 2023 Wiley-VCH GmbH.

Keywords

  • imino-Stetter reaction
  • indole
  • radiosynthesis
  • rucaparib
  • Suzuki-Miyaura borylation

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis of a Pinacol Boronate Precursor for [18F]Rucaparib Radiosynthesis'. Together they form a unique fingerprint.

Cite this