144809-27-8

Usage

Uses

Used in Pharmaceutical Industry:
5-Ethyl-2-pyridineethanol Tosylate is used as an intermediate in the synthesis of Pioglitazone impurities. Pioglitazone is a medication used to treat type 2 diabetes, and the compound plays a crucial role in the development and production of this drug. Its application in the pharmaceutical industry is essential for the creation of effective treatments for diabetes patients.
Additionally, as an intermediate, 5-Ethyl-2-pyridineethanol Tosylate may have potential applications in the development of other pharmaceutical compounds, although the provided materials do not specify these uses.

Upstream product

• 5223-06-3 5-ethyl-2-(2-hydroxyethyl)pyridine 
• 98-59-9 p-toluenesulfonyl chloride 
• 104-90-5 5-ethyl-2-methyl-pyridine 

Downstream Products

• 952188-00-0 5-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]benzyl}-3-[2-(5-ethyl-pyridin-2-yl)ethyl]-1,3-thiazolidine-2,4-dione 
• 16106-44-8 potassium tosylate 
• 1574532-69-6 Sodium (4-(2-(5-ethylpyridin-2-yl)ethoxy)phenyl)(hydroxy)methanesulfonate 
• 136401-69-9 5-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]benzylidene}-2,4-thiazolidinedione 
• 105355-27-9 Pioglitazone 
• 5408-74-2 5-ethyl-2-vinyl-pyridine 
• 114393-97-4 4-[2-(5-ethylpyridyl)ethoxy]benzaldehyde 
• 85583-54-6 4-[2-(5-ethyl-2-pyridyl)ethoxy]nitrobenzene 
• 312690-32-7 2-[1-{4-[2-(5-Ethyl-pyridin-2-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-4-(3aR,7aS)-octahydro-isoindol-2-yl-4-oxo-butyric acid ethyl ester 
• 312689-76-2 2-{4-[2-(5-Ethyl-pyridin-2-yl)-ethoxy]-benzyl}-4-(3aR,7aS)-octahydro-isoindol-2-yl-4-oxo-butyric acid ethyl ester 

Relevant academic research and scientific papers

Development of an improved and scalable process for 2-(5-ethylpyridin-2-yl) ethan-1-ol: Solvent-free reaction and recycling of the starting material 5-ethyl-2-picoline

The main objective of this exercise was to develop a more efficient process for 2-(5-ethylpyridin-2-yl)ethan-1-ol (1), which is the key intermediate in the synthesis of pioglitazone hydrochloride. This process not only features the yield improvement of (1) by optimizing reaction variables in solvent-free conditions but also highlights improving the mass efficiency of 5-ethyl-2-picoline (2), thereby reducing the effluent load per kilogram of the intermediate.

5-(4-HYDROXYBENZYL)THIAZOLIDINE-2,4-DIONE AS INTERMEDIATE FOR SYNTHESIS OF THIAZOLIDINEDIONE BASED COMPOUNDS AND PROCESS FOR PREPARING THE SAME

The present invention relates to 5-(4-hydroxybenzyl)thiazolidine-2,4-dione represented by the following Chemical Formula [1], which is useful as an intermediate for synthesis of thiazolidinedione based compounds, a method for preparing the compound, and a method for preparing pioglitazone or pioglitazone hydrochloride, which is a thiazolidinedione based drug and useful in treating and preventing diabetes, using the 5-(4-hydroxybenzyl)thiazolidine-2,4-dione represented by Chemical Formula [1] as an intermediate:

PROCESS FOR THE PREPARATION OF 5-[[4-[2-(5-ETHYL-2-PYRIDINYL)ETHOXY]PHENYL] METHYL]-2,4-THIAZOLIDINEDIONE

A process for the preparation of 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione (formula 1) comprising a. reacting diazonium salt of 4-[2-(5-Ethyl-2-pyridyl) ethoxy] amino- benzene, compound of formula 2, with acrylamide, aqueous HX (wherein X is Br or Cl), under meerwein arylation conditions to yield compound of formula 3; b. condensing compound of formula 3 with thiourea to obtain compound of formula 4; and c. converting compound of formula 4 to compound of formula 1.

Production of benzaldehyde compounds

A method of producing a compound represented by the formula: STR1 wherein R1 stands for hydrogen or an optionally substituted alkyl or acyl group, which comprises reacting a compound represented by the formula: STR2 wherein R1 is of the same meaning as defined above, and R2 stands for an optionally halolgenated alkyl group or an optionally substituted phenyl group with a compound represented by the formula: STR3 in a lower alcohol in the presence of an alkali metal or alkaline earth metal carbonate; the compound (III) being useful as starting compounds for producing thiazolidinedione derivatives having hypoglycemic and hypolipidemic activities.