337904-76-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Pyridinecarbonitrile,6-(1-methylethyl)-(9CI) is used as a building block for the synthesis of various pharmaceuticals. Its unique structure and functional groups make it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 2-Pyridinecarbonitrile,6-(1-methylethyl)-(9CI) serves as a key intermediate in the production of various agrochemicals. Its incorporation into these compounds can enhance their effectiveness in pest control and crop protection.
Used in Chemical Compound Production:
2-Pyridinecarbonitrile,6-(1-methylethyl)-(9CI) is utilized as an intermediate in the synthesis of a wide range of chemical compounds. Its versatility and reactivity contribute to the creation of diverse products across various industries.

Upstream product

• 65257-53-6 2-isopropylpyridine N-oxide 
• 7677-24-9 trimethylsilyl cyanide 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 644-98-4 2-isopropylpyridine 
• 1068-55-9 isopropylmagnesium chloride 
• 33252-29-8 6-chloro-pyridine-2-carbonitrile 
• 100-71-0 2-Ethylpyridine 

Downstream Products

• 900816-50-4 2-acetyl-6-isopropylpyridine 
• 337904-77-5 6-isopropylpicolinic acid 
• 153646-84-5 (6-isopropyl-2-pyridyl)methanol 
• 900816-56-0 2-[1-(2,6-diisopropylphenylimino)ethyl]-6-isopropylpyridine N-oxide 
• 900816-54-8 (2,6-diisopropylphenyl)[1-(6-isopropylpyridin-2-yl)ethylidene]amine 

Relevant academic research and scientific papers

Enantioselective synthesis of tunable chiral pyridine-aminophosphine ligands and their applications in asymmetric hydrogenation

A small library of tunable chiral pyridine-aminophosphine ligands were enantioselectively synthesized based on chiral 2-(pyridin-2-yl)-substituted 1,2,3,4-tetrahydroquinoline scaffolds, which were obtained in high yields and with excellent enantioselectivities via ruthenium-catalyzed asymmetric hydrogenation of 2-(pyridin-2-yl)quinolines. The protocol features a wide substrate scope and mild reaction conditions, enabling scalable synthesis. These chiral P,N ligands were successfully applied in the Ir-catalyzed asymmetric hydrogenation of benchmark olefins and challenging seven-membered cyclic imines including benzazepines and benzodiazepines. Excellent enantio- and diastereoselectivity (up to 99% ee and >20:1 dr), and/or unprecedented chemoselectivity were obtained in the asymmetric hydrogenation of 2,4-diaryl-3H-benzo[b]azepines and 2,4-diaryl-3H-benzo[b][1,4]diazepines.

Enantioselective Pd(II)-Catalyzed Intramolecular Oxidative 6- endo Aminoacetoxylation of Unactivated Alkenes

A novel asymmetric 6-endo aminoacetoxylation of unactivated alkenes by palladium catalysis, which yields chiral β-acetoxylated piperidines with excellent chemo-, regio- and enantioselectivities under very mild reaction conditions, has been established herein by employing a new designed pyridine-oxazoline (Pyox) ligand. Importantly, introducing a sterically bulky group into the C-6 position of Pyox is crucial to enhance the reactivity of the aminoacetoxylation of alkenes.

Iron-Catalyzed Isopropylation of Electron-Deficient Aryl and Heteroaryl Chlorides

Traditional methods for the preparation of secondary alkyl-substituted aryl and heteroaryl chlorides challenge both selectivity and functional group tolerance. This contribution describes the use of statistical design of experiments to develop an effective procedure for the preparation of isopropyl-substituted (hetero)arenes with minimal isopropyl to n-propyl isomerization. The reaction tolerates electronically diverse aryl chloride coupling partners, with excellent conversion observed for strongly electron-deficient aromatic rings, such as esters and amides. Electron-rich systems, including methyl- and methoxy-substituted aryl chlorides, were found to be less reactive. Furthermore, the reaction was found to be most successful when heteroaryl chlorides were submitted to the cross-coupling protocol. By mapping substituent effects on reaction selectivity, we were able to show that electron-deficient aryl chlorides are essential for efficient coupling, and use electronic structure calculations to predict the likelihood of successful coupling through the estimation of the electron affinity of each aryl chloride. Moderate isolated yields were achieved with selected aryl chlorides, and moderate to good isolated yields were obtained for all the heteroaryl chlorides coupled. Excellent selectivity was observed when a 2,6-dichloroquinoline was used, allowing mono-substitution on a challenging substrate. (Figure presented.).

C?H Cyanation of 6-Ring N-Containing Heteroaromatics

Heteroaromatic nitriles are important compounds in drug discovery, both for their prevalence in the clinic and due to the diverse range of transformations they can undergo. As such, efficient and reliable methods to access them have the potential for far-reaching impact across synthetic chemistry and the biomedical sciences. Herein, we report an approach to heteroaromatic C?H cyanation through triflic anhydride activation, nucleophilic addition of cyanide, followed by elimination of trifluoromethanesulfinate to regenerate the cyanated heteroaromatic ring. This one-pot protocol is simple to perform, is applicable to a broad range of decorated 6-ring N-containing heterocycles, and has been shown to be suitable for late-stage functionalization of complex drug-like architectures.

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of formula (I) and the N-oxides, salts, and stereoisomers, wherein each dashed line represents an optional double bond; X is N, CH and where X bears a double bond it is C; R1 is -OR7, -NH-SO2R8; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, C3-7cycloalkyl; R4 is aryl or Het; n is 3, 4, 5, or 6; R5 is halo, C1-6alkyl, hydroxy, C1-6alkoxy, phenyl, or Het; R6 is C1-6alkoxy, or dimethylamino; R7 is hydrogen; aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; R8 is aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; aryl is phenyl optionally substituted with one, two or three substituents; Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, and being optionally substituted with one, two or three substituents ; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I). Bioavailable combinations of the inhibitors of HCV of formula (I) with ritonavir are also provided.

Chelate [2-(iminoethyl)pyridine N-oxide]metal complexes - Synthesis and structural comparison with their chemically related 2-(iminoethyl)pyridine- derived systems

The N,O-chelate ligands 2-(iminoethyl)pyridine N-oxide (2a) and 2-(iminoethyl)-6-isopropylpyridine N-oxide (2b) were prepared by conventional synthetic routes, the latter involving a variant of the Reissert-Henze reaction. Treatment of 2a with FeCl2 resulted in a deoxygenation reaction of the ligand and formation of the salt (bis{2-(iminoethyl)-pyridine}FeCl] +[FeCl4]- (18a). In contrast, the reaction of 2a with PdCl2 or CoCl2 cleanly furnished the six-membered chelate [κN,O-2(iminoethyl)pyridine N-oxide]MCl2 complexes (19a, M = Pd) or (20a, M = Co), respectively, which were both characterised by X-ray diffraction. Treatment of 2b with [NiBr2 (dme)], followed by crystallisation from THF, gave the complex [κN,O-2b)NiBr2(THF)] (21b), which features a distorted trigonal-bipyramidal coordination geometry of the central metal atom. The reaction of 2a with [NiBr2(dme)] gave the structurally related complex [(κN,O-2a)NiBr2(κO-2a)] (21a). The N,O-chelate Pd complex 19a was shown to be an active catalyst for the Suzuki coupling reaction. The ligand systems 2a,b and their related 2-(iminoethyl)-pyridines 3a,b and a variety of metal complexes of ligands 3 were also prepared and characterised for comparison by X-ray diffraction. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

DRUG DISCHARGE PUMP INHIBITORS

A medicament for preventive and/or therapeutic treatment of a microbial infection having an activity of eliminating resistance of a microorganism with acquired resistance to an antimicrobial agent, which comprises as an active ingredient a compound represented by the following general formula (I), a physiologically acceptable salt thereof, or a hydrate thereof: wherein R1 and R2 independently represent hydrogen atom, a halogen atom, carboxyl group and the like; J1 represents a 5- or 6-membered heteroaromatic ring; W1 represents -CH=CH-, -C≡C-, -CH2CH2- and the like; A1 represents phenylene group, pyridinediyl group, furandiyl group and the like; G1 represents oxygen atom, carbonyl group, ethynyl group and the like; p represents an integer of from 0 to 3; G2 represents phenylene group, furandiyl group, tetrahydrofurandiyl group and the like; G3 represents -CH2- or single bond; m and n represent an integer of 0 or 1; and Q1 represents an acidic group.

A series of non-quinoline cysLT1 receptor antagonists: SAR study on pyridyl analogs of Singulair

The structure-activity relationship of a series of styrylpyridine analogs of MK-0476 (montelukast, Singular) is described. This work has led to the identification of a number of potent and orally active cysLT1 receptor (LTD4 receptor) antagonists including 2ab (L-733,321) as an optimized candidate.