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A kind of preparation method of n-(2-pyridine/pyrimidinyl) indole derivative

A technology of indole derivatives and pyrimidine derivatives, which is applied in the field of preparation of N-indole derivatives, can solve the problems of poor reaction regioselectivity, narrow substrate application range, and harsh equipment requirements, and achieve short reaction time and post-production The effect of processing green and easy post-processing

Active Publication Date: 2020-05-05
HUAQIAO UNIVERSITY
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Problems solved by technology

The above method generally has the following problems: 1) poor reaction regioselectivity and many by-products; 2) expensive transition metals are used; 3) copper acetate is used as an oxidizing agent, which is not environmentally friendly; 4) the reaction temperature is high and the requirements for equipment are harsh; 5 ) substrate has a narrow scope of application

Method used

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  • A kind of preparation method of n-(2-pyridine/pyrimidinyl) indole derivative
  • A kind of preparation method of n-(2-pyridine/pyrimidinyl) indole derivative
  • A kind of preparation method of n-(2-pyridine/pyrimidinyl) indole derivative

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Experimental program
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Effect test

Embodiment 1

[0020] Preparation of 2-phenyl-1-(2-pyridyl)indole:

[0021]

[0022] Under nitrogen, add 0.2 mmol of N-phenylpyridin-2-amine, 0.3 mmol of (1-alkenyl azido)benzene, 0.01 mmol of palladium trifluoroacetate, 0.4 mmol of potassium persulfate, and 0.08 mmol of triethylenediamine Put it into a reaction tube containing 1mL-1.5mL of toluene, place it in an oil bath at 75°C, and react for 24h. Remove the heat source from the reaction and cool to room temperature. The reaction solution was filtered through celite, concentrated, and purified by column chromatography to obtain 48 mg of the target product with a yield of 89%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.62 (dd, J=4.9, 1.2Hz, 1H), 7.68 (d, J=4.4Hz, 1H), 7.66 (dd, J=5.0, 1.6Hz, 1H), 7.60 (ddd, J=7.8 , 2.0Hz, 1H), 7.31-7.19(m, 8H), 6.88(d, J=8.0Hz, 1H), 6.80(s, 1H); 13 C NMR (101MHz, CDCl 3 )δ152.1, 149.2, 139.9, 138.5, 137.7, 132.7, 132.7, 128.7, 128.3, 127.4, 123.0, 122.0, 12...

Embodiment 2

[0024] Preparation of 2-phenyl-1-(2-pyrimidinyl)indole:

[0025]

[0026] Under nitrogen, add 0.2mmol of N-phenylpyrimidin-2-amine, 0.3mmol of (1-alkenyl azido)benzene, 0.01mmol of palladium trifluoroacetate, 0.4mmol of potassium persulfate, and 0.08mmol of triethylenediamine Put it into a reaction tube containing 1mL-1.5mL of toluene, place it in an oil bath at 75°C, and react for 24h. Remove the heat source from the reaction and cool to room temperature. The reaction solution was filtered through celite, concentrated, and purified by column chromatography to obtain 36 mg of the target product with a yield of 66%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.67(d, J=4.8Hz, 1H), 8.13(d, J=8.1Hz, 1H), 7.65(d, J=7.7Hz, 1H), 7.30-7.22(m, 3H), 7.10( d, J=4.8Hz, 1H), 6.81(s, 1H); 13 C NMR (101MHz, CDCl 3 )δ158.2, 140.5, 138.1, 133.9, 129.3, 129.3, 128.15, 128.1, 127.1, 123.5, 122.1, 120.7, 117.6, 112.8, 108.2.

Embodiment 3

[0028] Preparation of 5-methyl-2-phenyl-1-(2-pyridyl)indole:

[0029]

[0030] Under nitrogen, 0.2mmol of N-(p-tolyl)pyridin-2-amine, 0.3mmol of (1-alkenyl azido)benzene, 0.01mmol of palladium trifluoroacetate, 0.4mmol of potassium persulfate, triethylenediamine 0.08mmol was added to a reaction tube containing 1mL-1.5mL toluene, placed in an oil bath at 75°C, and reacted for 24h. The reaction was removed from the heat source and cooled to room temperature. The reaction solution was filtered through celite, concentrated, and purified by column chromatography to obtain 47 mg of the target product with a yield of 83%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.58(d, J=4.9Hz, 1H), 7.57(d, J=8.4Hz, 1H), 7.52(dd, J=6.9Hz, 1H), 7.42(s, 1H), 7.24-7.17( m, 4H), 7.12(dd, J=7.4, 4.9Hz, 1H), 7.03(d, J=8.4Hz, 1H), 6.82(d, J=8.0Hz, 1H), 6.71(s, 1H), 2.44(s, 3H); 13 C NMR (101MHz, CDCl 3 ) δ152.2, 149.0, 139.9, 137.6, 136.9, 132.8, 130.5, 12...

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Abstract

The invention discloses a preparation method of an N-(2-pyridyl / pyrimidyl)indole derivative. The preparation method of the N-(2-pyridyl / pyrimidyl)indole derivative comprises the following steps: mixing a 2-substituted phenylaminopyridine / pyrimidine derivative, an alkenyl azide compound, a catalyst, an oxidizing agent, alkali and an organic solvent uniformly, heating to 60 to 80 DEG C under nitrogen or air, performing a cyclization reaction for 18 to 24 hours, cooling to room temperature after the reaction, and performing concentration and column chromatographic purification to obtain the N-(2-pyridyl / pyrimidyl)indole derivative. By the preparation method, the N-(2-pyridyl / pyrimidyl)indole derivative with various substituent groups which cannot be synthesized according to other methods canbe synthesized; furthermore, the used raw materials are easily available, the yield is high, the reaction condition is mild, the reaction time is short, the substrate range is wide, the reaction specificity is high and aftertreatment is simple, convenient 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 N-(2-pyridine / pyrimidinyl) indole derivatives. Background technique [0002] N-(2-pyridine / pyrimidinyl)indole derivatives are a class of widely used intermediates in organic synthesis, and have important application values ​​in natural products, pharmaceutical production, and organic synthesis. Therefore, the study of new preparation methods for multi-substituted indoles has important application value and has attracted the attention of researchers in related fields. [0003] Traditional methods for the synthesis of N-(2-pyridine / pyrimidinyl) indole derivatives include Fischer indole synthesis; Larock indole synthesis; transition metal-catalyzed 2-multisubstituted phenylaminopyridine derivatives with 1,2-disubstituted Hydrocarbon cyclization reactions, etc. The above method generally has the following problems: 1) poor reaction regi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07D403/04
CPCC07D401/04C07D403/04
Inventor 王连会崔秀灵揭亮华
Owner HUAQIAO UNIVERSITY
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