FeCl 3 -catalyzed oxidative decarboxylation of aryl/heteroaryl acetic acids: preparation of selected API impurities

There is an ever-increasing demand for impurity compounds for use in impurity profiling as regulatory agencies seek information during registration. Herein, we report the FeCl -catalyzed oxidative decarboxylation of aryl- and heteroaryl acetic acids to the corresponding carbonyl compounds. A variety...

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Veröffentlicht in:Organic & biomolecular chemistry 2020-11, Vol.18 (41), p.8459-8466
Hauptverfasser: Gangadurai, Chinnakuzhanthai, Illa, Giri Teja, Reddy, D Srinivasa
Format: Artikel
Sprache:eng
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Zusammenfassung:There is an ever-increasing demand for impurity compounds for use in impurity profiling as regulatory agencies seek information during registration. Herein, we report the FeCl -catalyzed oxidative decarboxylation of aryl- and heteroaryl acetic acids to the corresponding carbonyl compounds. A variety of useful aldehydes and ketones were prepared in a simple one-pot transformation by employing an environmentally benign, low-cost, and readily available iron salt. The utility of this method has been demonstrated by preparing five valuable API impurities including a multi-gram-scale synthesis of ketorolac impurity B for the first time.
ISSN:1477-0520
1477-0539
DOI:10.1039/D0OB01790F