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A kind of preparation method of 1,2,3-trisubstituted-5-trifluoromethylpyrrole derivative

A technology of trifluoromethylpyrrole and trifluoromethyl, which is applied in the field of 1, achieves the effects of high yield, green post-treatment, and wide substrate range

Active Publication Date: 2022-03-04
HUAQIAO UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, developing methods to introduce trifluoromethyl groups has become a new challenge in the field of organic chemistry

Method used

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  • A kind of preparation method of 1,2,3-trisubstituted-5-trifluoromethylpyrrole derivative
  • A kind of preparation method of 1,2,3-trisubstituted-5-trifluoromethylpyrrole derivative
  • A kind of preparation method of 1,2,3-trisubstituted-5-trifluoromethylpyrrole derivative

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Experimental program
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Effect test

Embodiment 1

[0029] Preparation of (1,2-diphenyl-5-(trifluoromethyl)-1H-pyrrol-3-yl)(phenyl)methanone

[0030]

[0031] 0.1 mmol of 1,3-diphenyl-1,3-propanedione, (E)-3-(dimethyl(oxo)-λ 6 -Sulfinyl)-1,1,1-trifluoro-N-phenylpropane-2-imine 0.2mmol, lithium bromide 0.1mmol and acetonitrile 0.5mL were added to a 15mL reaction tube and placed in an oil bath at 80°C , reacted for 24h; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was successively washed with anhydrous Na 2 SO 4 Drying, filtration, concentration and TLC purification gave 31.1 mg of the target product in a yield of 79%. The NMR and high-resolution mass spectrometry characterizations of the target product obtained in this embodiment are as follows: 1 H NMR (500MHz, Chloroform-d) δ7.76 (dd, J=8.2, 1.4Hz, 2H), 7.47-7.40(m, 1H), 7.36-7.27(m, 5H), 7.22-7.18(m, 2H ), 7.13(s, 1H), 7.12-7.08(m, 1H), 7.10-7.03(m, 4H); 13 C NMR (126MHz, Chlorof...

Embodiment 2

[0033] Preparation of (1-phenyl-2-(m-tolyl)-5-(trifluoromethyl)-1H-pyrrol-3-yl)(m-tolyl)methanone

[0034] 0.1 mmol of 1,3-di-m-tolylpropane 1,3-dione, (E)-3-(dimethyl(oxo)-λ 6 Add 0.2mmol of -sulfinyl)-1,1,1-trifluoro-N-phenylpropane-2-imine, 0.1mmol of lithium bromide and 0.5mL of acetonitrile into a 15mL reaction tube and place in an oil bath at 80°C , reacted for 24h; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was successively washed with anhydrous Na 2 SO 4 Drying, filtration, concentration and purification by TLC gave 28.3 mg of the target product with a yield of 65%. The NMR and high-resolution mass spectrometry characterizations of the target product obtained in this embodiment are as follows: 1 H NMR (500MHz, Chloroform-d) δ7.54(dt, J=6.5, 2.0Hz, 1H), 7.50(s, 1H), 7.37-7.27(m, 3H), 7.20(t, J=6.1 Hz, 4H), 7.15(s, 1H), 6.93(t, J=7.6Hz, 1H), 6.88(d, J=7.6Hz, 1H), 6.85-6.78(m...

Embodiment 3

[0036] Preparation of 4-methoxyphenyl)(2-(4-methoxyphenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrrol-3-yl)methanone

[0037]0.1 mmol of 1,3-bis(4-methoxyphenyl)propane-1,3-dione, (E)-3-(dimethyl(oxo)-λ 6 Add 0.2mmol of -sulfinyl)-1,1,1-trifluoro-N-phenylpropane-2-imine, 0.1mmol of lithium bromide and 0.5mL of acetonitrile into a 15mL reaction tube and place in an oil bath at 80°C , reacted for 24h; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was successively washed with anhydrous Na 2 SO 4 Drying, filtration, concentration and purification by TLC gave 31.9 mg of the target product with a yield of 71%. The NMR and high-resolution mass spectrometry characterizations of the target product obtained in this embodiment are as follows: 1 H NMR (500 MHz, Chloroform-d) δ7.84-7.76 (m, 2H), 7.37-7.28 (m, 3H), 7.20 (dd, J=7.8, 1.9Hz, 2H), 7.07 (s, 1H) , 7.02-6.97(m, 2H), 6.86-6.82(m, 2H), 6.63-6....

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Abstract

The invention discloses a preparation method of 1,2,3-trisubstituted-5-trifluoromethylpyrrole derivatives, comprising the following steps: (1) combining 1,3-diketone derivatives, sulfur ylides, additives and After mixing the organic solvents, react at 60-100°C for 12-24h; (2) Dilute the material obtained in step (1) with ethyl acetate, and then wash with water to separate the organic phase; (3) Dilute the material obtained in step (2) The obtained organic phase is dried, filtered, concentrated and subjected to column chromatography or thin layer chromatography to obtain the 1,2,3-trisubstituted-5-trifluoromethylpyrrole derivative. The present invention has good regioselectivity in the construction of 1,2,3-trisubstituted-5-trifluoromethylpyrrole derivatives; the raw materials used in the present invention are easy to obtain, the yield is high, the reaction conditions are mild, the reaction time is short, and the substrate Wide range, strong reaction specificity, easy post-processing and green.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 1,2,3-trisubstituted-5-trifluoromethylpyrrole derivatives. Background technique [0002] Pyrrole and its derivatives are one of the basic organic structural units. At the same time, they are widely found in natural products and are also important intermediates in organic synthesis. They are widely used in many fields such as medicine, pesticides, and functional materials. Therefore, it is possible to obtain drugs with better potential drug effects by modifying the functional group of the pyrrole ring. For example, trifluoromethyl has unique steric and electronic properties, and it is generally believed that it may significantly improve the pharmacokinetics and pharmacodynamics of lead compounds, and is considered to be a priority structural motif in the development of new drugs. Therefore, developing methods to introduce trifluoromet...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/333C07D409/14C07D207/34
CPCC07D207/333C07D409/14C07D207/34
Inventor 程国林文思
Owner HUAQIAO UNIVERSITY
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