Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of synthetic method of 2-fluoroindole compound

A synthesis method and compound technology, applied in the directions of steroids, chemical instruments and methods, organic chemistry, etc., can solve the problems of harsh reaction conditions, troublesome, high synthesis cost, etc., and achieve the effect of simple operation and simple raw material synthesis.

Active Publication Date: 2022-04-05
HUAQIAO UNIVERSITY
View PDF9 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods are relatively cumbersome, the reaction conditions are harsh, and transition metals need to be used at the same time, and the synthesis cost is relatively high, which seriously limits its application.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of synthetic method of 2-fluoroindole compound
  • A kind of synthetic method of 2-fluoroindole compound
  • A kind of synthetic method of 2-fluoroindole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The reaction formula of the present embodiment is as follows:

[0029]

[0030] (1) Add 0.2mmol o-dimethylaminochalcone, 0.6mmol ethyl bromodifluoroacetate and 0.6mmol potassium phosphate into a pressure-resistant sealed reaction tube, remove the air, fill it with nitrogen, and inject 2mL of acetonitrile into the Stir the reaction at 90°C for 12 hours in a pressure-resistant sealed reaction tube, and use TLC and GC to track the reaction process to determine the specific reaction time;

[0031] (2) The material obtained in step (1) is taken out from the above-mentioned pressure-resistant sealed reaction tube, after cooling to room temperature, ethyl acetate is added to fully mix, then filtered and washed with ethyl acetate in sequence, and combined to obtain an organic phase;

[0032] (3) spin dry the acetonitrile in the organic phase that step (2) gains, then purify through silica gel column and eluent (petroleum ether: dichloromethane=5: 1) rinse, obtain 2-fluoromet...

Embodiment 2

[0038] The reaction formula of the present embodiment is as follows:

[0039]

[0040] (1) Add 0.2mmol o-dimethylaminonaphthylchalcone, 0.6mmol ethyl bromodifluoroacetate and 0.6mmol potassium phosphate into a pressure-resistant sealed reaction tube, remove the air, fill with nitrogen, and add 2mL of acetonitrile Inject into a pressure-resistant sealed reaction tube, stir and react at 90°C for 12 hours, track with TLC and GC during the reaction to determine the specific reaction time;

[0041] (2) The material obtained in step (1) is taken out from the above-mentioned pressure-resistant sealed reaction tube, after cooling to room temperature, ethyl acetate is added to fully mix, then filtered and washed with ethyl acetate in sequence, and combined to obtain an organic phase;

[0042] (3) spin dry the acetonitrile in the organic phase that step (2) gains, then purify through silica gel column and eluent (petroleum ether: dichloromethane=5: 1) rinse, obtain 2-fluoromethyl-3 ...

Embodiment 3

[0048] Under the same reaction conditions as in Example 1 and Example 2, the universality and good functional group compatibility of the substrate of the present invention were studied, and the o-dimethylaminochalcone and o-dimethylaminonaphthalene in the above-mentioned examples were Kichalcones are replaced as follows:

[0049]

[0050]

[0051] The corresponding products obtained are as follows:

[0052]

[0053]

[0054]

[0055] The NMR data of the above products are as follows:

1528

[0056]1H NMR (500MHz, Chloroform-d) δ8.15(d, J=8.5Hz, 2H), 7.69(d, J=8.5Hz, 2H), 7.65-7.61(m, 2H), 7.53(d, J= 7.8Hz, 1H), 7.48(t, J=7.5Hz, 2H), 7.43-7.39(m, 1H), 7.23-7.19(m, 2H), 7.16(dt, J=8.1, 4.1Hz, 1H), 4.35(s, 2H), 3.64(s, 3H).

[0057] 13C NMR(126MHz,Chloroform-d)δ196.28,145.76,139.91,135.06,130.62,129.13,128.97,128.24,127.28,127.27,121.27,121.24,120.46,118.90,118.85,108.85,32.99,32.96,27.98.

[0058] 19F NMR (471MHz, Chloroform-d) δ-138.82.

1276

[0059] 1H N...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for synthesizing 2-fluoroindole compounds, which comprises the following steps: (1) adding o-aminochalcone compounds, ethyl bromodifluoroacetate, alkali and an organic solvent into a pressure-resistant seal In the reaction vessel, stir the reaction at 50-100°C for 10-15h under a nitrogen atmosphere; (2) After the material obtained in step (1) is cooled to room temperature, add ethyl acetate and mix thoroughly, and then successively pass through filtration and ethyl acetate (3) spin-drying the organic solvent in the organic phase obtained in step (2), and then purifying and rinsing with an eluent to obtain the 2-fluoroindole compound. The present invention can efficiently realize the synthesis of 2-fluoroindole compounds by using o-aminochalcone compounds as raw materials under mild conditions, with the participation of nitrogen, adding alkali and solvent.

Description

technical field [0001] The invention belongs to the technical field of organic materials, and in particular relates to a synthesis method of 2-fluoroindole compounds. Background technique [0002] Fluorine atoms or fluorine-containing groups have unique physical and chemical properties, such as acidity and alkalinity, lipid solubility and metabolic stability, etc. In addition, fluorine-containing compounds can also control reactivity and stereochemistry in asymmetric reactions. In the past decade, the introduction of fluorine atoms into bioactive scaffolds has received increasing attention in the fields of organic and medicinal chemistry. [0003] Indole, as a very important heterocyclic skeleton, widely exists in natural products, bioactive compounds and other functional molecules. [0004] In the prior art, 2-fluoroindole compounds are relatively difficult to synthesize, and there are few synthetic methods at present. The main method is to synthesize indole compounds fir...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/30C07J9/00C07F17/00
CPCC07D209/30C07J9/00C07F17/02
Inventor 宋秋玲苏建科朱舒娴
Owner HUAQIAO UNIVERSITY