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A method for synthesizing 2-fluoro-n-substituted aryl acetamides

An arylacetamide and compound technology, which is applied in the field of synthesizing 2-fluoro-N-substituted arylacetamide compounds, can solve the problems of unrealized C-H activation, low efficiency and the like, and achieves high atom utilization and substrate utilization. Wide adaptability and mild reaction conditions

Active Publication Date: 2020-06-30
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, general amides are generally regarded as weakly coordinated oxygen atom donors, which are less efficient in palladium catalysis, especially the C-H activation of distal weakly coordinated phenylacetamides has not yet been realized.

Method used

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  • A method for synthesizing 2-fluoro-n-substituted aryl acetamides
  • A method for synthesizing 2-fluoro-n-substituted aryl acetamides
  • A method for synthesizing 2-fluoro-n-substituted aryl acetamides

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Experimental program
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Effect test

Embodiment 1

[0035]

[0036] Add N-substituted phenylacetamide (37.8mg, 0.2mmol), palladium chloride (3.6mg, 0.02mmol), N-fluorobenzenesulfonimide (126.1mg, 0.4mmol) into a closed reaction vessel, Silver nitrate (13.6mg, 0.08mmol), 1,2-dichloroethane (2.0mL), and the reaction mixture was stirred at 45°C, followed by TLC detection, and the reaction was complete within 24 hours. The reaction was stopped, the mixture was diluted with ethyl acetate, the solvent was removed under reduced pressure, and the residue was subjected to column chromatography [GF254 silica gel; 200-300 mesh; the developing solvent was V (petroleum ether) / V (ethyl acetate) = 3 / 1] After separation and purification, the eluate containing the product was collected, and the solvent was evaporated from the eluate to obtain 33.1 mg of pure 2-fluoro-N-substituted phenylacetamide, with a yield of 80%.

Embodiment 2

[0038]

[0039] Add 2-methyl-N-substituted phenylacetamide (40.6mg, 0.2mmol), palladium chloride (3.6mg, 0.02mmol), N-fluorobenzenesulfonimide (126.1mg , 0.4mmol), silver nitrate (13.6mg, 0.08mmol), 1,2-dichloroethane (2.0mL), the reaction mixture was stirred and reacted at 60°C, followed by TLC detection, and the reaction was complete within 24h. The reaction was stopped, the mixture was diluted with ethyl acetate, the solvent was removed under reduced pressure, and the residue was subjected to column chromatography [GF254 silica gel; 200-300 mesh; the developing solvent was V (petroleum ether) / V (ethyl acetate) = 3 / 1] After separation and purification, the eluent containing the product was collected, and the solvent was evaporated from the eluent to obtain 40.2 mg of pure 6-fluoro-2-methyl-N-substituted phenylacetamide, with a yield of 91%.

Embodiment 3

[0041]

[0042] Add m-methyl-N-substituted phenylacetamide (40.6mg, 0.2mmol), palladium chloride (3.6mg, 0.02mmol), N-fluorobenzenesulfonimide (126.1mg, 0.4mmol), silver nitrate (13.6mg, 0.08mmol), 1,2-dichloroethane (2.0mL), the reaction mixture was stirred and reacted at 45°C, followed by TLC detection, and the reaction was complete within 24h. The reaction was stopped, the mixture was diluted with ethyl acetate, the solvent was removed under reduced pressure, and the residue was subjected to column chromatography [GF254 silica gel; 200-300 mesh; the developing solvent was V (petroleum ether) / V (ethyl acetate) = 3 / 1] After separation and purification, the eluent containing the product was collected, and the solvent was evaporated from the eluent to obtain 35.8 mg of pure 2-fluoro-5-methyl-N-substituted phenylacetamide, with a yield of 81%.

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Abstract

The invention provides a method for synthesizing a 2-fluoro-N-substituted aryl acetamide compound. The method comprises the following steps that a N-substituted aryl acetamide compound reacts at 20 to150 DEG C under the condition of existence of palladium catalysts, fluorinated reagents and additives; TLC tracking detection is performed until the reaction is thoroughly performed; through aftertreatment, the compound shown as a formula II is obtained; the amide substituent ortho-position high-selectivity aryl hydrocarbon bond direct fluorination can be mildly realized. The method has the advantages that the reaction conditions are mild; the operation is simple; the substrate applicability is high; the fluoridation selectivity is high, and the like. High application study values are realized.

Description

technical field [0001] The invention relates to a method for synthesizing 2-fluoro-N-substituted arylacetamides with mild reaction conditions, simple operation, good substrate adaptability and high fluorination selectivity. Background technique [0002] Due to the special properties of fluorine atoms, the introduction of fluorine atoms into aromatic compounds can significantly increase the stability of the compound, and at the same time improve its fat solubility and hydrophobicity, promote its absorption and delivery in the body, and change its physiological effects. Fluorine medicines and pesticides have the characteristics of less dosage, low toxicity, high efficacy, and strong metabolism in terms of performance, which makes it account for an increasing proportion of new medicines and pesticides. In addition, fluorine-containing dyes, fluorine-containing surfactants, fluorine-containing fabric finishing agents, and fluorine-containing coatings have become high value-added...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/185C07B39/00
CPCC07B39/00C07D295/185
Inventor 宁兴倩娄绍杰许丹倩徐振元
Owner ZHEJIANG UNIV OF TECH
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