120427-96-5Relevant academic research and scientific papers
Preparation method of 4-(2-bromoethyl)-1, 3-dihydro-2H-indole-2-ketone
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Paragraph 0032; 0037-0040; 0045-0048; 0053; 0054, (2021/05/05)
The invention provides a preparation method of 4-(2-bromoethyl)-1, 3-dihydro-2H-indole-2-ketone, and the preparation method of the 4-(2-bromoethyl)-1, 3-dihydro-2H-indole-2-ketone is characterized in that the 4-(2-bromoethyl)-1, 3-dihydro-2H-indole-2-ketone is prepared by taking o-bromoethyl benzaldehyde as an initial raw material and carrying out a series of reactions. The raw materials are cheap and easy to obtain, the product yield and purity are high, and the method has excellent economic and environment-friendly benefits.
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
Matera, Carlo,Quadri, Marta,Pelucchi, Silvia,De Amici, Marco,Dallanoce, Clelia
, p. 1139 - 1144 (2014/06/24)
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 %).
PROCESS FOR PURIFICATION OF ROPINIROLE
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Page/Page column 22, (2010/02/13)
The invention discloses an improved process for the purification of ropinirole hydrochloride by dissolving or suspending crude ropinirole base or its pharmaceutically acceptable salt in a suitable solvent, reacting with a nitrogenous base to form an imine derivative, optionally treating the reaction mixture with a base to adjust the pH, and isolating purified ropinirole hydrochloride. The invention also provides for a pharmaceutical composition comprising pure ropinirole hydrochloride as active ingredient.
Indolinone derivatives as protein kinase/phosphatase inhibitors
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, (2008/06/13)
The present invention relates to certain 2-indolinone compounds which modulate the activity of protein kinases (“PKs”) and phosphatases. The compounds of this invention are therefore useful in treating disorders related to abnormal PK activity. Pharmaceutical compositions comprising these compounds, methods of treating diseases utilizing pharmaceutical compositions comprising these compounds and methods of preparing them are also disclosed.
Development of large-scale syntheses of ropinirole in the pursuit of a manufacturing process
Hayler, John D.,Howie, Simon L. B.,Giles, Robert G.,Negus, Alan,Oxley, Paul W.,Walsgrove, Timothy C.,Whiter
, p. 3 - 9 (2013/09/08)
Two plant syntheses of ropinirole {4-[2-(di-n-propyIamino)-ethyl]-1,3-dihydro-2H-indolin-2-one hydrochloride, SK&F-101468-A} using the ferric chloride mediated cyclisation of β-nitrostyrenes to form 3-chlorooxindoles as the key step are described. The first synthesis suffered the severe limitation of the final-step chemistry being nonselective in the reaction between di-n-propylamine and the bromide precursor to ropinirole as both substitution and elimination pathways were promoted and by-product formation at a level of 40% resulted. This problem was rectified in the latter synthesis by the more selective reaction between di-n-propylamine and the sulfonate ester precursor promoting ropinirole formation to a level of 88%. This second synthesis is now used as the commercial route, and problems (and their solutions) identified during the development of this route are now described. The identification of novel by-products which enabled the Sommelet oxidation step to be optimised is also reported. A unimolecular decomposition mechanism during hydrolysis of the hexaminium salt to form the key benzaldehyde intermediate is proposed and substantiated with experimental data.
Some synthetic approaches to ropinirole (SK and F 101468-A): A potent dopamine receptor agonist
Hayler,Howie,Giles,Negus,Oxley,Walsgrove,Walsh,Dagger,Fortunak,Mastrocola
, p. 875 - 882 (2007/10/02)
Three new routes to ropinirole (SK and F 101468-A, 1) are described each involving the preparation of 3-chlorooxindole intermediates of type 3 from β-nitrostyrenes as the pivotal step. The superiority of sulphonate esters 17a-c as direct precursors to 1 over the bromide 11 is also described.
Process for preparing substituted isoindolinone derivatives
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, (2008/06/13)
This invention relates to an improved process for the preparation of substituted indolinone derivatives using reductive cyclization conditions.
