35853-55-5

Usage

Uses

Used in Pharmaceutical Industry:
Bis[2,8-di(trifluoromethyl)quinolin-4-yl-2-pyridyl] ketone is used as an intermediate in the synthesis of Mefloquine Hydrochloride (M207052), a labeled quinoline methanol antimalarial agent. Its role in the synthesis process is crucial for the development of effective treatments against malaria, a disease that affects millions of people worldwide.
bis[2,8-di(trifluoromethyl)quinolin-4-yl-2-pyridyl] ketone's specific structural features allow it to contribute to the overall effectiveness of Mefloquine Hydrochloride, which is known for its ability to combat Plasmodium parasites responsible for malaria. By being a part of the synthesis process, bis[2,8-di(trifluoromethyl)quinolin-4-yl-2-pyridyl] ketone plays a significant role in the pharmaceutical industry's efforts to combat this global health issue.

InChI:InChI=1/C17H8F6N2O/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11/h1-8H

Upstream product

• 83012-12-8 α-(2-Pyridyl)-2,8-bis(trifluoromethyl)-4-quinolylacetonitrile 
• 138058-60-3 α-Hydroxy-α-(2-pyridyl)-2,8-bis(trifluoromethyl)-4-quinolylacetonitrile 
• 123590-69-2 4-<(tert-butyldimethylsilyl)(2-pyridyl)methoxy>-2,8-bis(trifluoromethyl)quinoline 
• 68496-04-8 [2,8-bis(trifluoromethyl)quinolin-4-yl]pyridin-2-ylmethanol 
• 17624-36-1 2-pyridyllithium 
• 941279-81-8 2,4-dimethyl-3-(pyridin-2-ylmethyl)pentan-3-ol 
• 35853-50-0 2,8-bis-(trifluoromethyl)-quinoline-4-carboxylic acid 
• 35853-45-3 (2,8-bis-trifluoromethyl)-4-bromoquinoline 
• 83012-13-9 2,8-bis-(trifluoromethyl)-4-chloro-quinoline 
• 2739-97-1 pyridine-2-acetonitrile 
• 123559-29-5 4-(2-pyridylmethoxy)-2,8-bis(trifluoromethyl)quinoline 
• 6959-47-3 2-chloromethylpyridine hydrochloride 
• 35853-41-9 2,8-bis(trifluoromethyl)quinolin-4-ol 

Downstream Products

• 51744-85-5 (+)-threo-mefloquine hydrochloride 
• 68682-28-0 (R)-2-((S)-(2,8-bis(trifluoromethyl)quinolin-4-yl)(hydroxy)methyl)piperidin-1-ium chloride 
• 49752-90-1 (+/-)-mefloquine 
• 51773-92-3 mefloquine hydrochloride 

Relevant academic research and scientific papers

A straightforward mid high yielding synthesis of mefloquine - II

A new practical and high yielding synthesis of mefloquine (1) is described. Heteroarylation of 2-pyridylacetonitrile (2) gave the key intermediate 2-pyridyl-4-quinolylacetonitrile 4, which, on reaction with m-chloroperbenzoic acid, gave unexpectedly the cyanhydrine 5 The later, after base treatment afforded quantitatively the ketone 6.

Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen

The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP-MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit.

Use of (+)mefloquine for the treatment of malaria

Use of (+)-(11R,2′S)-α-2-piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol or a pharmaceutically acceptable salt thereof substantially free of its (?)-enantiomer in the manufacture of a medicament having reduced side-effect compared to the racemic (±)-(R*,S*)-α-2-piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol for treating or preventing malaria in a subject. A method of treating or preventing malaria with reduced side-effects comprising administration of (+)-(11R,2′S)-α-2-piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol or a pharmaceutically acceptable salt thereof substantially free of its (?)-enantiomer.

ONE POT SYNTHESIS OF [2, 8-BIS (TRIFLUOROMETHYL)-4- QUINOLINYL]2-PYRIDINYLMETHANONE, A MEFLOQUINE INTERMEDIATE

The present invention provides a simple single step process for the preparation of [2,8-bis (trifluoromethyl)-4-quinolinyl]-2 -pyridinylmethanone, comprising the step of condensing a halo-quinoline with an alpha-picolyl derivatives in the presence of a solvent, a base and a phase transfer catalyst at ?10° C. to +90° C.