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publicationDate 2007-12-27-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber WO-2007148141-A1
titleOfInvention Process for the synthesis of benzylidene rosiglitazone base
abstract Process for the synthesis of 5-{4-[N-methyl-N- (2-pyridyl)-amino-ethoxy]- 5 benzylidene}-thiazolidine-2, 4-dione (INN name: benzylidene-rosiglitazone) of formula (I), which consist of the following steps: (I) Step a) reaction of 2-chloro-pyridine and 2-(N-methylamino)-ethanol Step b) reaction of the obtained compound of formula (III) with 4- 0 fluorobenzaldehyde Step c) reaction of the obtained compound of formula (IV) with thiazolidine-2, 4-dione. (III), ((IV). characterized by - dissolving 4-{2-[N-methyl-N- (2-pyridyl) amino]-ethanol of formula (III) obtained in Step a) in toluene and using it in Step b) without isolation; - reacting the solution of compound of formula (III) in toluene in Step b) with 4-fluorobenzaldehyde in the presence of aqueous alkali hydroxide solution and phase transfer catalyst at 25-50 °C; - reacting the solution of the benzaldehyde derivative of formula (IV) obtained in Step b) in toluene in Step c) and isolating the desired product.
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