This paper describes a practical approach to the preparation of 4-(2-hydroxyethyl)indolin-2-one, a key intermediate in the synthesis of dopaminergic agonists such as ropinirole—a drug used in the treatment of Parkinson’s disease and restless legs syndrome—and of two sets of protein kinase inhibitors. The sequence starts from commercially available 2-(2-methyl-3-nitrophenyl)acetic acid, which is converted in five steps into the desired target compound. This procedure offers a convenient alternative route to existing methodologies, given its milder reaction conditions, ease of implementation, and its overall yield (59 %).

A convenient synthesis of 4-(2-hydroxyethyl)indolin-2-one, a useful intermediate for the preparation of both dopamine receptor agonists and protein kinase inhibitors / C. Matera, M. Quadri, S. Pelucchi, M. De Amici, C. Dallanoce. - In: MONATSHEFTE FÜR CHEMIE. - ISSN 0026-9247. - 145:7(2014 Jul), pp. 1139-1144. [10.1007/s00706-014-1211-z]

A convenient synthesis of 4-(2-hydroxyethyl)indolin-2-one, a useful intermediate for the preparation of both dopamine receptor agonists and protein kinase inhibitors

C. Matera;M. Quadri;S. Pelucchi;M. De Amici;C. Dallanoce
2014-07

Abstract

This paper describes a practical approach to the preparation of 4-(2-hydroxyethyl)indolin-2-one, a key intermediate in the synthesis of dopaminergic agonists such as ropinirole—a drug used in the treatment of Parkinson’s disease and restless legs syndrome—and of two sets of protein kinase inhibitors. The sequence starts from commercially available 2-(2-methyl-3-nitrophenyl)acetic acid, which is converted in five steps into the desired target compound. This procedure offers a convenient alternative route to existing methodologies, given its milder reaction conditions, ease of implementation, and its overall yield (59 %).
D-2/D-3 agonists; Heterocycles; Indolin-2-ones; One-pot synthesis; Ropinirole; Synthetic improvement
Settore CHIM/08 - Chimica Farmaceutica
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/236639
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