147754-12-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluoro-2-methylbenzonitrile is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique chemical structure allows it to serve as a building block in the development of new medications, potentially contributing to the treatment of various health conditions.
Used in Chemical Synthesis:
In the chemical industry, 4-Fluoro-2-methylbenzonitrile is utilized as an organic intermediate. Its versatile structure makes it a valuable component in the synthesis of a wide range of chemical products, including specialty chemicals, agrochemicals, and other industrial applications.
Overall, 4-Fluoro-2-methylbenzonitrile is a versatile compound with applications in both the pharmaceutical and chemical industries, primarily due to its unique chemical structure and its role as an intermediate in the synthesis of various products.

InChI:InChI=1/C8H6FN/c1-6-4-8(9)3-2-7(6)5-10/h2-4H,1H3

Upstream product

• 452-63-1 2-Bromo-5-fluorotoluene 
• 544-92-3 copper(I) cyanide 
• 80141-91-9 (4-fluoro-2-methylphenyl)methanol 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 66256-28-8 4-fluoro-1-iodo-2-methylbenzene 
• 557-21-1 dicyanozinc 
• 459-57-4 4-fluorobenzaldehyde 
• 73963-98-1 zinc cyanide 

Downstream Products

• 1062612-70-7 4-fluoro-2-(3-methyl-but-3-enyl)-benzonitrile 
• 1436378-68-5 N-[(1S)-1-{[(3S)-4-(3-hydroxyphenyl)-3-methylpiperazin-1-yl]-methyl}-2-methylpropyl]-2-methyl-4-(3-methylphenoxy)benzamide 
• 65538-23-0 2-methyl-4-(3-methylphenoxy)benzoic acid 
• 1485536-93-3 2-(dibromomethyl)-4-fluorobenzonitrile 
• 421552-12-7 2-(bromomethyl)-4-fluorobenzonitrile 
• 928201-46-1 Trelagliptin hydrochloride 

Relevant academic research and scientific papers

Practical CuCl/DABCO/4-HO-TEMPO-catalyzed oxidative synthesis of nitriles from alcohols with air as oxidant

A mild and efficient methodology for the direct oxidative synthesis of nitriles from easily available alcohols and aqueous ammonia by employing CuCl/DABCO/4-HO-TEMPO as the catalysts is described. This protocol uses the air as a green oxidant and aqueous ammonia as the nitrogen source at room temperature. A variety of aryl, heterocyclic and allylic alcohols are smoothly converted into the corresponding nitriles in good to excellent yields.

A PROCESS FOR THE PREPARATION OF 4-FLUORO-2-METHYLBENZONITRILE

The present invention provides a process for the preparation of 4-fluoro-2- methylbenzonitrile of Formula (II), and its use for the preparation of trelagliptin or its salts. The present invention provides an efficient, simple, and commercially friendly pr

New trelagliptin preparation process

The present invention provides a trelagliptin preparation process, which comprises that: 1) a compound 4 and a compound 5 are adopted as raw materials, and are subjected to a condensation reaction in an organic solvent in the presence of an alkali to obtain a compound 6; 2) the compound 6 reacts with an acid HA in an organic solvent to remove the t-butyloxy carbonyl so as to obtain a trelagliptin.HA salt; and 3) the trelagliptin.HA salt is subjected to alkali neutralization treatment and purification to obtain the trelagliptin, wherein the reaction route is defined in the specification. According to the present invention, in the improved preparation process, the 2-site amino of the compound 5 is protected by the t-butyloxy carbonyl, such that the selectivity of the nucleophilic substitution reaction is improved, and the impurity production caused by primary amine substitution is avoided so as to improve the nucleophilic substitution yield and improve the trelagliptin purity.

Synthetic method of trelagliptin, trelagliptin synthesized through method and trelagliptin synthesis intermediate

The invention discloses a synthetic method of trelagliptin, trelagliptin synthesized through the method and a trelagliptin synthesis intermediate. The synthetic method of trelagliptin comprises the following steps: 1, taking 2-hydroxymethyl-4-fluorobenzonitrile as a starting raw material, and conducting a chlorination reaction, so that 2-chloromethyl-4-fluorobenzonitrile is obtained; 2, taking the 2-chloromethyl-4-fluorobenzonitrile as an intermediate, and conducting a condensation reaction, so that 2-[(6-chlorine-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidyl)methyl]-4-fluorobenzonitrile is obtained; 3, taking the 2-[(6-chlorine-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidyl)methyl]-4-fluorobenzonitrile as an intermediate, and conducting an ammonolysis reaction, so that trelagliptin alkali is obtained. By means of the method, use of high-toxicity copper cyanide is avoided, safety of the synthesis process is improved, environment friendliness is achieved, the formed chloro intermediate is more stable, and no irritation is caused.

Cobalt-Catalyzed Electrophilic Cyanation of Arylzinc Halides with N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS)

The cobalt-catalyzed cross-coupling of organozinc bromides with N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) is described. The same cobalt catalyst, cobalt(II) bromide, was used for both the synthesis of the organozinc species and the cross-coupling reaction. However in this case, a catalytic amount of zinc dust is necessary in the second step to release the low-valent cobalt. Under these mild conditions, moderate to excellent yields of different benzonitriles were obtained.

Highly practical synthesis of nitriles and heterocycles from alcohols under mild conditions by aerobic double dehydrogenative catalysis

A mild, aerobic, catalytic process for obtaining nitriles directly from alcohols and aqueous ammonia is described. The reaction proceeds via a dehydrogenation cascade mediated by catalytic CuI, bpy, and TEMPO in the presence of O2. The substrate scope is broad including various functionalized aromatic and aliphatic alcohols. This protocol enabled the one-pot synthesis of various biaryl heterocycles directly from commercially available alcohols.

Design and synthesis of pyrimidinone and pyrimidinedione inhibitors of dipeptidyl peptidase IV

The discovery of two classes of heterocyclic dipeptidyl peptidase IV (DPP-4) inhibitors, pyrimidinones and pyrimidinediones, is described. After a single oral dose, these potent, selective, and noncovalent inhibitors provide sustained reduction of plasma DPP-4 activity and lowering of blood glucose in animal models of diabetes. Compounds 13a, 27b, and 27j were selected for development.

DIPEPTIDYL PEPTIDASE INHIBITORS

Methods of making compounds of the formula (I) wherein the variables are as defined herein. Also, methods of making compounds that may be used to inhibit dipeptidyl peptidase.

ADMINISTRATION OF DIPEPTIDYL PEPTIDASE INHIBITORS

Pharmaceutical compositions comprising 2-[6-(3-Amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl]-4-fluoro-benzonitrile and pharmaceutically acceptable salts thereof are provided as well as kits and articles of manufacture comprising the pharmaceutical compositions as well as methods of using the pharmaceutical compositions.

POLYMORPHS OF SUCCINATE SALT OF 2-[6-(3-AMINO-PIPERIDIN-1-YL)-3-METHYL-2,4-DIOXO-3,4-DIHYDRO-2H-PYRIMIDIN-1-YLMETHY]-4-FLUOR-BENZONITRILE AND METHODS OF USE THEREFOR

Compositions comprising the succinate salt of 2-[6-(3-Amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl]-4-fluoro-benzonitrile (referred to herein as Compound I) which has the formula: (I) wherein the Compound I is present in one or more polymorphic forms. Also provided are novel methods for the preparation of the polymorphs of Compound I, and kits and articles of manufacture of the compositions, and methods of using the compositions to treat various diseases.