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1-methyl-2-cyano-3-aliphatic substituted pyrrole compound synthesis method

A synthetic method and aliphatic technology, applied in the direction of organic chemistry, can solve the problems of low Ecoscale index, impossibility of industrial promotion and application, and low atom utilization rate, so as to improve environmental index, improve atom utilization rate and efficiency, and increase yield and the effect of purity

Active Publication Date: 2020-02-04
HUNAN BIOLOGICAL & ELECTROMECHANICAL POLYTECHNIC
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In view of the existence of atomic utilization in the preparation method of 1-methyl-2-cyano-3-aliphatic substituted azocene compounds (N-methyl-2-cyano-3-aliphatic azocene compounds) in the prior art Low, low reaction efficiency, low Ecoscale index, incapable of industrial promotion and application, etc., the purpose of the present invention is to provide a new reaction mechanism of 1-methyl-2-cyano-3-aliphatic substituted nitrogen The compound method aims to provide a new synthetic method with high atomic efficiency, high yield, low cost, environmental friendliness, no need for chromatographic purification, and favorable for industrial production application

Method used

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Experimental program
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Effect test

Embodiment 1～3

[0055] Following examples 1~3 all react by following reaction equation:

[0056]

[0057] The specific operation steps are: in a 50mL pressure-resistant tube, add octyne (30mmol), trimethylcyanosilane (30mmol, 2.97g), N,N-dimethylformamide (30mmol, 2.19g), iodine ammonium chloride (9mmol, 1.30g), and the resulting mixture was stirred and reacted at 100°C for about 3 hours. After the reaction, add 15ml of saturated sodium sulfite for washing, extract 3 times with 15mL of ethyl acetate, combine the extracts, concentrate the extracts in vacuo, dry in vacuo and calculate the weight.

Embodiment 1

[0059] raw material: Target product:

[0060] 3-hexyl-1-methyl-1H-pyrrole-2-carbonitrile:

[0061] Yield: 92%.

[0062] Yellowish green oil;

[0063] 1 H NMR (500MHz, CDCl 3 )δ6.68(d, J=2.5Hz, 1H), 5.99(d, J=2.5Hz, 1H), 3.71(s, 3H), 2.56(t, J=7.7Hz, 2H), 1.59-1.50( m,4H),1.31-1.30(m,2H),1.30-1.29(m,2H),0.89(t,J=6.7Hz,3H).

[0064] 13 C NMR (126MHz, CDCl 3 )δ137.61, 127.19, 114.09, 109.26, 103.05, 35.37, 31.73, 30.65, 29.01, 26.85, 22.74, 14.23.

[0065] IR (neat, cm –1 )ν2970, 2260, 1555, 1320, 1041, 886, 761, 738.

[0066] HRMS (ESI) calcd for C 9 h 19 N 2 [M+H] + :191.1543, found 191.1546.

Embodiment 2

[0068] raw material: Target product:

[0069] 3-benzyl-1-methyl-1H-pyrrole-2-carbonitrile:

[0070] Yield: 82%.

[0071] 1 H NMR (500MHz, CDCl 3 )δ7.29(t, J=7.5Hz, 2H), 7.25-7.19(m, 3H), 6.69 (d, J=2.4Hz, 1H), 5.96(d, J=2.4Hz, 1H), 3.91( s,2H),3.73(s,3H).

[0072] 13 C NMR (126MHz, CDCl 3 )δ140.23, 135.72, 128.67, 128.64, 127.49, 126.41, 113.81, 109.81, 103.30, 35.46, 33.16.

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Abstract

The invention discloses a 1-methyl-2-cyano-3-aliphatic substituted pyrrole compound synthesis method, which comprises: carrying out a three-component addition reaction on terminal aliphatic hydrocarbon, trimethylcyano silane and N,N-dimethylformamide according to an equal chemical molar weight ratio under the catalytic action of ammonium iodide to generate a 1-methyl-2-cyano-3-aliphatic substituted pyrrole compound; and after the reaction is finished, washing the reaction system with saturated sodium sulfite, and extracting the water phase with ethyl acetate to obtain the high-purity 1-methyl-2-cyano-3-aliphatic substituted pyrrole compound. According to the invention, the method is good in product selectivity, high in yield, simple in separation process, low in catalyst cost, environmentally friendly and beneficial to industrial production and application.

Description

technical field [0001] The invention belongs to the technical field of synthesis of organic intermediates, and in particular relates to a synthesis method of 1-methyl-2-cyano-3-aliphatic substituted azocene compounds. Background technique [0002] The cyano group (CN-), its small size, only 1 / 8 of the methyl group, has a strong electron-withdrawing property, in addition, it also has a good hydrogen bond acceptor, and can form with various functional groups such as carbonyl and halogen Bioelectronic isosteres, so the introduction of cyano groups into small drug molecules can change the physical and chemical properties of small molecules, which may enhance the interaction between small drug molecules and target proteins and improve drug efficacy. Not only that, the introduction of cyano group may also serve as a metabolic blocking site, inhibit the oxidative metabolism of small molecules, and improve the metabolic stability of compounds in vivo. [0003] It is possible to mod...

Claims

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Application Information

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IPC IPC(8): C07D207/34
CPCC07D207/34
Inventor 马玉捷徐晓林张朝辉聂莹文星星
Owner HUNAN BIOLOGICAL & ELECTROMECHANICAL POLYTECHNIC
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