221148-38-5

Usage

Uses

Used in Pharmaceutical Industry:
(3-Fluoro-phenyl)-propynoic acid methyl ester is used as an intermediate in the synthesis of various pharmaceuticals. Its unique reactivity and properties allow for the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical sector, (3-Fluoro-phenyl)-propynoic acid methyl ester is utilized as a precursor in the production of agrochemicals. Its fluorinated structure can enhance the performance and selectivity of these compounds, leading to more effective pest control and crop protection.
Used in Dye Industry:
(3-Fluoro-phenyl)-propynoic acid methyl ester is used as a building block in the synthesis of dyes. The presence of the fluorine atom can impart specific color characteristics and improve the stability of the dyes, making them suitable for various applications, such as textiles and printing inks.
Used in Organic Chemical Reactions:
As a reagent, (3-Fluoro-phenyl)-propynoic acid methyl ester is employed in various organic chemical reactions. Its unique properties can be exploited to facilitate specific transformations, leading to the formation of new compounds with potential applications in various industries.
Used in Production of Other Chemical Compounds:
(3-Fluoro-phenyl)-propynoic acid methyl ester is also used in the production of other chemical compounds. Its versatility and reactivity make it a valuable component in the synthesis of a wide range of products, further expanding its applications across different sectors.

Upstream product

• 221148-37-4 1-(2,2-Dibromo-vinyl)-3-fluoro-benzene 
• 79-22-1 methyl chloroformate 
• 2561-17-3 1-ethynyl-3-fluoro-benzene 
• 1121-86-4 1-Fluoro-3-iodobenzene 
• 922-67-8 propynoic acid methyl ester 
• 74-88-4 methyl iodide 
• 558-13-4 carbon tetrabromide 
• 456-48-4 3-Fluorobenzaldehyde 
• 1711-07-5 3-fluorobenzoyl chloride 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 267235-92-7 2-(3-fluoro-phenyl)-6-trifluoromethyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid methyl ester 
• 221148-39-6 2-(3-fluoro-phenyl)-6-methoxy-pyrazolo[1,5-b]pyridazine-3-carboxylic acid methyl ester 
• 705-83-9 3-(m-fluorophenyl)-propiolic acid 
• 852818-41-8 C₁₂H₈FN₃O 
• 221148-50-1 6-difluoromethoxy-2-(3-fluoro-phenyl)-3-(4-methanesulfonyl-phenyl)-pyrazolo[1,5-b]pyridazine 
• 221148-43-2 3-bromo-6-difluoromethoxy-2-(3-fluoro-phenyl)-pyrazolo[1,5-b]pyridazine 
• 221148-40-9 2-(3-fluoro-phenyl)-6-methoxy-pyrazolo[1,5-b]pyridazine-3-carboxylic acid 
• 221148-41-0 3-bromo-2-(3-fluoro-phenyl)-6-methoxy-pyrazolo[1,5-b]pyridazine 
• 221148-42-1 6-difluoromethoxy-2-(3-fluoro-phenyl)-pyrazolo[1,5-b]pyridazine 
• 781674-47-3 2-(3-fluoro-phenyl)-pyrazolo[1,5-b]pyridazine-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Asymmetric Transfer Hydrogenation of gem-Difluorocyclopropenyl Esters: Access to Enantioenriched gem-Difluorocyclopropanes

Catalytic enantioselective access to disubstituted functionalized gem-difluorocyclopropanes, which are emerging fluorinated motifs of interest in medicinal chemistry, was achieved through asymmetric transfer hydrogenation of gem-difluorocyclopropenyl este

Oxidant- and additive-free simple synthesis of 1,1,2-triiodostyrenes by one-pot decaroboxylative iodination of propiolic acids

A metal- and oxidant-free facile synthesis of a range of 1,1,2-triiodostryrene derivatives has been developed which utilizes a simple decarboxylative triiodination of propiolic acids using molecular iodine and sodium acetate in a one-pot manner. Electron-

Rhodium(III)-Catalyzed Redox-Neutral Cascade [3 + 2] Annulation of N-Phenoxyacetamides with Propiolates via C-H Functionalization/Isomerization/Lactonization

A Rh(III)-catalyzed cascade [3 + 2] annulation of N-phenoxyacetamides with propiolates under mild conditions using the internal oxidative O-N bond as the directing group has been achieved. This catalytic system provides a regio- and stereoselective access to benzofuran-2(3H)-ones bearing exocyclic enamino motifs with exclusive Z configuration selectivity, acceptable to good yields and good functional group compatibility. Mechanistic investigations by experimental and density functional theory studies suggest that a consecutive process of C-H functionalization/isomerization/lactonization is likely to be involved in the reaction.

Salt-Free Strategy for the Insertion of CO2 into C?H Bonds: Catalytic Hydroxymethylation of Alkynes

A copper(I) catalyst enables the insertion of carbon dioxide into alkyne C?H bonds by using a suitable organic base with which hydrogenation of the resulting carboxylate salt with regeneration of the base becomes thermodynamically feasible. In the presence of catalytic copper(I) chloride/4,7-diphenyl-1,10-phenanthroline, polymer-bound triphenylphosphine, and 2,2,6,6-tetramethylpiperidine as the base, terminal alkynes undergo carboxylation at 15 bar CO2 and room temperature. After filtration, the ammonium alkynecarboxylate can be hydrogenated to the primary alcohol and water at a rhodium/molybdenum catalyst, regenerating the amine base. This demonstrates the feasibility of a salt-free overall process, in which carbon dioxide serves as a C1 building block in a C?H functionalization.

Palladium-Catalyzed Ylidyl-Carbonylation of Aryl Halides to Produce α-Acylphosphoranes

An efficient synthesis of α-acylphosphoranes by palladium-catalyzed carbonylation of aryl iodides with carbon monoxide and stabilized phosphonium ylides has been developed. Featuring 44 examples, the protocol displayed a wide substrate scope under mild reaction conditions, showcasing its potential in synthetic organic chemistry.

Application and scope of Schreiber's gold(I)-catalyzed α-pyrone synthesis to ring a aromatic podolactones

Schreiber's gold(I)-catalyzed synthesis of α-pyrones was adapted to the total synthesis of a ring A aromatic podolactone, urbalactone. The scope of the acetylenic ester partner in the formation of α-pyrones was studied. The total synthesis features, as ke

Pyranone, thiopyranone, and pyridone inhibitors of phosphatidylinositol 3-kinase related kinases. Structure-activity relationships for DNA-dependent protein kinase inhibition, and identification of the first potent and selective inhibitor of the ataxia telangiectasia mutated kinase

Structure-activity relationships have been investigated for inhibition of DNA-dependent protein kinase (DNA-PK) and ATM kinase by a series of pyran-2-ones, pyran-4-ones, thiopyran-4-ones, and pyridin-4-ones. A wide range of IC50 values were observed for pyranones and thiopyranones substituted at the 6-position, with the 3- and 5-positions proving intolerant to substitution. Related pyran-2-ones, pyran-4-ones, and thiopyran-4-ones showed similar IC50 values against DNA-PK, whereas the pyridin-4-one system proved, in general, ineffective at inhibiting DNA-PK. Extended libraries exploring the 6-position of 2-morpholinopyran-4-ones and 2-morpholino- thiopyrano-4-ones identified the first highly potent and selective ATM inhibitor 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one (151C; ATM; IC50 = 13 nM) and revealed constrained SARs for ATM inhibition compared with DNA-PK. One of the most potent DNA-PK inhibitors identified, 2-(4-methoxyphenyl)-6- (morpholin-4-yl)pyran-4-one (16; DNA-PK; IC50 = 220 nM) effectively sensitized HeLa cells to the topoisomerase II inhibitor etoposide in vitro.

USE OF CYCLOOXYGENASE-2 INHIBITORS FOR THE TREATMENT OF DEPRESSIVE DISORDERS

The invention concerns the use of compounds of formula (I), (II) and (III): which are COX-2 (cyclooxygenase-2) inhibitors, and pharmaceutically acceptable salts or solvates thereof, for the treatment of depressive disorders in combination with an effective amount of a second component which is a selective serotonin reuptake inhibitor.

PYRAZOLOPYRIDINE DERIVATIVES AS SELECTIVE COX-2 INHIBITORS

The invention provides the compounds of formula (I) and pharmaceutically acceptable derivatives thereof wherein: R0 and R1 are independently selected from the group consisting of H, halogen, C1-6alkyl, C1-6alkoxy, and C1-6alkoxy substituted by one or more fluorine atoms; R2 is selected from the group consisting of H, C1-6alkyl, C1-6alkyl substituted by one or more fluorine atoms, C1-6alkoxy, C1-6hydroxyalkyl, SC1-6alkyl, C(O)H, C(O)C1-6alkyl, C1-6alkylsulphonyl, and C1-6alkoxy substituted by one or more fluorine atoms; and R3 is C1-6alkyl or NH2. Compounds of formula (I) are potent and selective inhibitors of COX-2 and are of use in the treatment of the pain, fever, inflammation of a variety of conditions and diseases.

2,6-Disubstituted pyran-4-one and thiopyran-4-one inhibitors of DNA-dependent protein kinase (DNA-PK)

6-Aryl-2-morpholin-4-yl-4H-pyran-4-ones and 6-aryl-2-morpholin-4-yl-4H-thiopyran-4-ones were synthesised and evaluated as potential inhibitors of the DNA repair enzyme DNA-dependent protein kinase (DNA-PK). Several compounds in each series exhibited super