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Ortho-position mono chlorine substituted N-aryl azaindole compound and synthetic method thereof

An aryl nitrogen compound technology, which is applied in the field of N-aryl azaindole and its synthesis, can solve the problems of environmental pollution, high toxicity of halogenated reagents, harsh reaction conditions, etc., and achieves good development prospects, good reactivity, Moderate effects

Inactive Publication Date: 2015-01-28
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] In summary, there are many methods for preparing aryl halides, but the regioselectivity of these reactions is not easy to control, and it is difficult to obtain monohalogenated products with high regioselectivity.
In some reactions, the reaction raw materials are limited, the halogenated reagents are more toxic and easy to cause environmental pollution, and the yield of some reactions is relatively low or the reaction conditions are relatively harsh, etc.

Method used

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  • Ortho-position mono chlorine substituted N-aryl azaindole compound and synthetic method thereof
  • Ortho-position mono chlorine substituted N-aryl azaindole compound and synthetic method thereof
  • Ortho-position mono chlorine substituted N-aryl azaindole compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: 1-(2-chlorophenyl)-1 H -pyrrole[2,3- b ] The preparation of pyridine

[0044] 1-(2-Chlorophenyl)-4-1 H -pyrrole[2,3- b ] pyridine adopts the following steps: 1. add 19.42 grams of 1-phenyl-1H-pyrrole [2,3- b ]pyridine, 0.62 g [RhCp * Cl 2 ] 2 , 58.00 g of copper trifluoroacetate, 7.40 g of lithium carbonate, 16.60 g of tert-butylisonitrile, 500 ml of 1,2-dichloroethane, heated to 130-140 °C. Use thin layer chromatography to track the reaction until the reaction raw materials disappear; ② After the reaction, add 3 mol / L ammonia solution to the system, extract the product with ethyl acetate, and remove the solvent with a rotary evaporator after drying to obtain the crude product ; ③ The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 20: 1) to obtain 17.61 grams of 1-(2-chlorophenyl)-4-1 H -pyrrole[2,3- b ] Pyridine, the productive rate is 77%.

[0045] –1 ): 3064, 1587, 1514, 1422, 1357, 1323, 1279, 797, 773,...

Embodiment 2

[0050] Example 2: 1-(2-chloro-4-methylphenyl)-1 H -pyrrole[2,3- b ] The preparation of pyridine

[0051] 1-(2-Chloro-4-methylphenyl)-1 H -pyrrole[2,3- b ] pyridine adopts the following steps: 1. add 20.83 grams of 1-(p-tolyl)-1 in 1000 milliliters of reactor H -pyrrole[2,3- b ]pyridine, 0.74 g [RhCp * Cl 2 ] 2 , 66.58 grams of copper trifluoroacetate, 8.88 grams of lithium carbonate, 19.09 grams of tert-butylisonitrile, 500 milliliters of 1,2-dichloroethane, heated to 130-140 °C. Use thin layer chromatography to track the reaction until the reaction raw materials disappear; ② After the reaction, add 3 mol / L ammonia solution to the system, extract the product with ethyl acetate, and remove the solvent with a rotary evaporator after drying to obtain the crude product ; ③ The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 20: 1) to obtain 17.23 grams of 1-(2-chloro-4-methylphenyl)-1 H -pyrrole[2,3- b ] Pyridine, the productive rate...

Embodiment 3

[0057] Embodiment three: 3-chloro-4-(1 H -pyrrole[2,3- b ]pyridine) the preparation of methyl benzoate

[0058] 1-(2-Chloro-4-methylphenyl)-1 H -pyrrole[2,3- b ] pyridine) methyl benzoate adopts the following steps: 1. add 25.23 grams of 4-(1 H -pyrrolo[2,3-b]pyridine) methyl benzoate, 0.86 g [RhCp * Cl 2 ] 2 , 69.48 grams of copper trifluoroacetate, 9.62 grams of lithium carbonate, 19.92 grams of tert-butylisonitrile, 500 milliliters of 1,2-dichloroethane, heated to 130-140 °C. Use thin layer chromatography to track the reaction until the reaction raw materials disappear; ② After the reaction, add 3 mol / L ammonia solution to the system, extract the product with ethyl acetate, and remove the solvent with a rotary evaporator after drying to obtain the crude product ; ③The crude product was purified by column chromatography (petroleum ether: ethyl acetate=20: 1) to obtain 20.36 grams of 3-chloro-4-(1 H -pyrrole[2,3- b ] pyridine) methyl benzoate, the productive rate is ...

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Abstract

The invention relates to an ortho-position mono chlorine substituted N-aryl azaindole compound and a synthetic method thereof. The structural formula of the compound is shown in the specification. R1 is hydrogen, methyl, methyl ester and acetyl; R2 = methoxy, cyclopropyl, bromine and phenyl; according to the method, raw materials are easy to obtain, and 1,2-dichloroethane as a halogen source has best reactivity under the catalysis of rhodium. The reaction has the advantages of simple operation, moderate reaction conditions, and environmental protection, the yield is up to 85%, and the compound has a good development prospect in industrial production.

Description

technical field [0001] The present invention relates to a N -Aryl azaindole and its synthesis method, especially one N -Ortho-monochlorinated compounds of arylazaindoles and methods for their synthesis. Background technique [0002] As a very important structural unit in bioactive molecules and drug molecules, organic halides have been widely concerned about their preparation methods. In recent years, direct C—H bond activation reactions involving transition metals have gradually become a hot topic in the synthesis of organic halides. Among these reactions, transition metals such as copper, palladium, and rhodium participate in catalyzed C—H bond activation reactions, which have the advantages of mild conditions, high selectivity, and high atom economy, showing great application potential in synthesis. In addition, indole and its derivatives have a wide range of biological activities and can be used to treat various diseases such as cardiovascular disease, diabetes and lu...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 许斌钱光印洪小虎刘秉新李莹莹
Owner SHANGHAI UNIV
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