13797-63-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Trifluoromethyl-3H-imidazo[4,5-b]pyridine is used as a building block for the synthesis of various biologically active molecules and pharmaceutical drugs. Its incorporation into drug molecules is driven by its ability to enhance the lipophilicity and metabolic stability of the resulting compounds, which are crucial for improving drug absorption, distribution, and overall efficacy.
The trifluoromethyl group's presence also endows the compound with specific physicochemical properties that are advantageous for drug development, such as increased lipophilicity and metabolic stability, which can lead to better pharmacokinetic profiles and potentially more effective therapeutic agents.

InChI:InChI=1/C7H4F3N3/c8-7(9,10)6-12-4-2-1-3-11-5(4)13-6/h1-3H,(H,11,12,13)

Upstream product

• 452-58-4 2,3-Diaminopyridine 
• 76-05-1 trifluoroacetic acid 
• 1522-22-1 1,1,1,5,5,5-hexafluoroacetylacetone 

Downstream Products

• 880177-62-8 C₁₃H₇F₃N₄O₂ 
• 1462875-27-9 4-[(6-chloro-3-pyridyl)methyl]-2-(trifluoromethyl)imidazo[4,5-b]pyridine 

Relevant academic research and scientific papers

Fe(OTf)3-catalyzed practical synthesis of 2-trifluoromethylarylimidazoles from o-arylenediamines and hexafluoroacetylacetone

An iron-catalyzed practical synthesis of 2-trifluoromethylarylimidazoles through condensation of o-arylenediamines and hexafluoroacetylacetone followed by intramolecular addition and C–C bond cleavage in one-pot has been developed. A series of title compounds were obtained with up to 99% yield. This method is quite practical and suitable for scalable preparation due to simple experimental procedure and readily available reagents.

N-SUBSTITUTED HETERO-BICYCLIC COMPOUNDS AND DERIVATIVES FOR COMBATING ANIMAL PESTS II

The invention relates to N-substituted hetero-bicyclic compounds of formula (I), to the enantiomers, diastereomers and salts thereof and to compositions comprising such compounds. The invention also relates to methods and uses of these N-substituted hetero-bicyclic compounds, and of compositions comprising thereof, for combating and controlling animal pests. Furthermore the invention relates also to pesticidal methods of applying such N-substituted heterobicyclic compounds. The N-substituted hetero-bicyclic compounds of the present invention are defined by the following formula I: wherein A, B, X, H et, R1, R2, W1, W2, W3 and W4 are defined as in the description.

Efficient syntheses of 2-fluoroalkylbenzimidazoles and -benzothiazoles

We report an efficient one-step route to 2-fluoroalkylbenzimidazoles and -benzothiazoles via the condensation of fluorinated carboxylic acids and aromatic diamines or aminothiophenols. Additionally, we describe the syntheses of fluoroalkyl-azabenzimidazoles, -purines, and -imidazolopyrazines. This method is high-yielding with broad scope and is operationally simple with potential application to parallel synthesis.

Synthesis of a series of trifluoromethylazoles and determination of pKa of acidic and basic trifluoromethyl heterocycles by 19F NMR spectroscopy

Trifluoroacetylation at the 5-position of 3,4-dihydro-2H-pyran and the 3-position of 4,5-dihydrofuran, followed by treatment with hydrazine, gave 3-(3-trifluoromethyl-1H-pyrazol-4-yl)propanol and 2-(3-trifluoromethyl-1H-pyrazol-4-yl)ethanol, respectively.In the latter case, an intermediate dimer was isolated.Isomeric 2-(3-trifluoromethyl-1H-pyrazol-5-yl)ethanol was formed by reaction of hydrazine with 6-benzyloxy-1,1,1-trifluorohex-3-yn-2-one and deprotection.Reaction of 3-benzyloxypropylamine with 2,5-bis(trifluoromethyl)-1,3,4-oxadiazole, followed by deprotection, afforded 3-propanol.A series of 2-trifluoromethyl-1H-benzimidazoles and 2-trifluoromethyl-3H-imidazopyridines were prepared by condensation of the appropriate ortho-arenediamine with trifluoroacetic acid.Analysis of the 19F NMR spectra of the trifluoromethylazoles and of 3-trifluoromethylpyridine in aqueous solution at different pHs enabled determination of pKa values.All the compounds evaluated had one or more pKa between 1 and 13, except the triazole.Several compounds were identified as having potential use in measuring pH in biological media by 19F NMR spectroscopy.