ArticleBeilstein journal of organic chemistry2018
Bromide-assisted chemoselective Heck reaction of 3-bromoindazoles under high-speed ball-milling conditions: synthesis of axitinib.
Article in Beilstein journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Arylation of Olefins with N-Unprotected Bromobisindole Ethanamines: Expanding the Scope of the Mizoroki-Heck Reaction.The Journal of organic chemistry · 2026Article
- Expanding Therapeutic Horizons with Indazole-Based Compounds: A Review of Anticancer, Antimicrobial, and Neuroprotective Applications.Medicinal chemistry (Shariqah (United Arab Emirates)) · 2026Review
- Mechanochemical Strategies Applied to the Late-Stage Modifications of Pharmaceutically Active Compounds.Angewandte Chemie (International ed. in English) · 2025Review
- Fluorinated and Non-Fluorinated 1,4-Diarylpyrazoles via MnOMolecules (Basel, Switzerland) · 2022Article
- Mechanochemical Friedel-Crafts acylations.Beilstein journal of organic chemistry · 2019Article
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Authors and funding
6 authors.
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Abstract
A mechanically-activated chemoselective Heck coupling for the synthesis of 3-vinylindazoles has been developed with the aid of catalytic amounts of TBAB and NaBr as both dehalogenation restrainer and grinding auxiliary. After tuning of the chemical conditions and mechanical parameters, a series of non-activated 3-bromoindazoles and a broad scope of olefins worked well to give the corresponding coupling products in good to excellent yields. A further application of this protocol was performed in a two-step mechanochemical Heck/Migita cross coupling, which provided a highly efficient route for the synthesis of axitinib.
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