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- Title
Scalable Preparation of 1‐Aminoethyl Oxindoles From Simple Benzaldehydes.
- Authors
Bürki, Cédric; Diethelm, Stefan; D'Aiuto, Fabio; Künzli, Marco; Mathieu, Gaëlle; Schmitt, Christine
- Abstract
Oxindoles are prevalent structures in natural products and pharmaceutically active molecules. To support structure–activity‐relationship (SAR) studies in a medicinal chemistry program, we developed a straightforward and scalable synthesis route to 1‐aminoethyl oxindole building blocks harboring various types of substituents. Our strategy relies on an intramolecular Buchwald–Hartwig amidation of a 2‐bromophenylacetic amide precursor. The cyclization substrates can be prepared from readily available benzaldehydes by ortho‐selective C(sp2)−H bromination followed by homologation to the corresponding phenylacetic acid derivatives. The process was optimized to allow for preparation of 246 g of one representative example.
- Subjects
OXINDOLES; PHENYLACETIC acid; PHARMACEUTICAL chemistry; INDUSTRIAL chemistry; ACID derivatives; BENZALDEHYDE; INDOLE
- Publication
Helvetica Chimica Acta, 2024, Vol 107, Issue 1, p1
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.202300188