75358-89-3

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-cyanopyridine-3-carboxylate is used as a pharmaceutical intermediate for the development of new drugs, leveraging its unique chemical structure to contribute to the synthesis of various medicinal compounds.
Used in Organic Synthesis:
In the field of organic synthesis, methyl 2-cyanopyridine-3-carboxylate serves as a valuable building block, enabling the creation of a wide range of organic molecules for research and commercial applications. Its presence of a cyanide and ester group makes it a versatile component in the synthesis of complex organic molecules.

InChI:InChI=1/C8H6N2O2/c1-12-8(11)6-3-2-4-10-7(6)5-9/h2-4H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 73112-09-1 2-cyanopyridine-3-carboxylic acid 
• 67-56-1 methanol 
• 124-63-0 methanesulfonyl chloride 
• 15905-18-7 1-oxy-nicotinic acid methyl ester 
• 7677-24-9 trimethylsilyl cyanide 
• 5860-70-8 2-Aminocarbonylnicotinic acid 
• 151-50-8 potassium cyanide 
• 91074-38-3 3-carbomethoxy-1-dimethylaminocarbonyloxypyridinium chloride 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 79-22-1 methyl chloroformate 
• 699-98-9 Pyridine-2,3-dicarboxylic anhydride 
• 55155-23-2 2,3-pyridinedicarboxylic acid chloride 

Downstream Products

• 93616-75-2 5-Amino-7-benzyl-7H-pyrido[2,3-d]pyridazin-8-one 
• 93617-20-0 1-[5-Oxo-5,6-dihydro-pyrrolo[3,4-b]pyridin-(7Z)-ylidene]-3-phenyl-urea 
• 81214-63-3 8-aminopyrido<2,3-d>pyridazine-5(6H)-one 
• 73112-09-1 2-cyanopyridine-3-carboxylic acid 
• 93616-73-0 6-Benzylamino-7-imino-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one 
• 93616-70-7 7-(Benzyl-hydrazono)-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one 
• 151509-02-3 methyl imidazo<1,5-a>pyridine-8-carboxylate 
• 151509-03-4 imidazo<1,5-a>pyridine-8-carbaldehyde 

Relevant academic research and scientific papers

Cyclic acyl amidines as unexpected C4-donors for fully substituted pyridine ring formation in the base mediated reaction with malononitrile

A new one-step, pseudo four-component approach for the synthesis of fully substituted pyridines via ring-opening of the cyclic acyl amidine of 3-amino-1H-isoindol-1-one and its aza-analogues during the reaction with malononitrile in the presence of sodium methoxide, followed by pyridine ring closure is reported. This method allows the one-step preparation of previously unknown 2-(pyridin-4-yl)(hetero)aryl carboxamides in good yields under mild reaction conditions.

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.

Efficient Synthesis of Nicotinic Acid Based Pseudopeptides Bearing an Amidoxime Function

The synthesis of nicotinic acid based amino acid units bearing an amidoxime function on the pyridine ring has been developed. The starting 2-cyanonicotinic acid was efficiently coupled with methyl esters of l-α-amino acids to afford intermediate 2-cyanopyridin-3-yl-containing pseudopeptides together with the tautomeric methyl esters of (2S)-2-(7-imino-5-oxo-5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl)alkanoic acids. Regioselective pyrrolidine ring opening of these esters occurred upon hydroxylamine hydrochloride treatment, giving rise to the open-chain pyridin-3-yl 2-amidoxime pseudopeptides bearing the same structure as amidoximes obtained by direct hydroxyamination of the corresponding cyano esters.

BIOREVERSABLE PROMOIETIES FOR NITROGEN-CONTAINING AND HYDROXYL-CONTAINING DRUGS

Disclosed are promoieties of the following formula which can be used to form prodrugs of nitrogen-containing or hydroxyl-containing drug or a pharmaceutically active agent: (I) and pharmaceutical compositions comprising the prodrugs.

1-ACYLOXYPYRIDINIUM ION: THE REACTIVE INTERMEDIATE IN A MODIFIED REISSERT-HENZE REACTION

Cyanation of 3-X-1-dimethylaminocarbonyloxypyridinium ions with trimethylsilanecarbonitrile or cyanide ion gives 3-methyl-2-pyridinecarbonitrile (ca.90percent) contaminated with 5-methyl-2-pyridinecarbonitrile (ca.10percent) when X = -CH3, and approximately equal amounts of the 3- and 5-X derivatives when X = -COOCH3.These product mixtures are identical to those obtained with the corresponding pyridine 1-oxides and dimethylcarbamoyl chloride in a modified Reissert-Henze reaction.

REGIOSELECTIVE CYANATION OF 3-SUBSTITUTED PYRIDINE 1-OXIDES

Cyanation of 3-X-pyridine 1-oxides with trimethylsilanecarbonitrile and dimethylcarbamoyl chloride occurs quantitatively to give 3-X-pyridinecarbonitriles in > 90percent isolated yields when X = -CH3, -OCH3, -OH and -Cl, and approximately equal amounts of the 3- and 5-X derivatives when X = -CN and -COOCH3.

PREPARATION AND STRUCTURAL ASSIGNMENTS OF SOME ISOMERIC 2,3-DISUBSTITUTED PYRIDINES

The preparation of several isomeric 2,3-disubstituted pyridine compounds are described and their spectroscopical data given.IR and NMR spectra of quinolinimide, reported by Distefano et al., are contradicted.The electron impact mass spectra are found to be useful in the differentiation between positional isomers.