Asymmetric N-pyridyl-2,2-diindyl compound and synthetic method thereof

A technology of pyridyl indole compound and indole compound, applied in the direction of organic chemistry, can solve the problems of harsh multi-step operation, difficult synthesis, difficult pre-functionalization, etc., and achieve high purity, high yield and narrow melting point range Effect

Inactive Publication Date: 2019-02-05
NANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The main disadvantages of this method are: the selective prefunctionalization of indole substrates is difficult, and the synthesis of 2-iodoindole and 2-indole boronic acid or 2-indole tin-based compounds and zinc compounds is extremely difficult, requiring extremely Harsh conditions and multi-step operations

Method used

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  • Asymmetric N-pyridyl-2,2-diindyl compound and synthetic method thereof
  • Asymmetric N-pyridyl-2,2-diindyl compound and synthetic method thereof
  • Asymmetric N-pyridyl-2,2-diindyl compound and synthetic method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] A kind of unsymmetrical N-pyridyl-2,2-indole compound, its general chemical structure formula is:

[0036]

[0037] The synthetic method of above-mentioned unsymmetrical N-pyridyl-2,2-indole compound, comprises the following steps:

[0038] (1) Under an air atmosphere, mix 0.2 mmol of N-pyridyl indole compound, 0.4 mmol of indole, [Cp*Co(CO)I 2 ]0.005mmol, AgSbF 6 0.02mmol, HOPiv 0.04mmol, Ag 2 O 0.4mmol, NaOAc 0.2mmol and 1,2-dichloroethane 2ml were mixed in a reaction tube, and heated in an oil bath at 100°C for 15h;

[0039] Described N-pyridyl indole compound structural formula is:

[0040] (2) After the reaction is completed, the reaction tube is cooled to room temperature, the reaction mixture is desalted, washed, concentrated, and purified to obtain the target product N-pyridyl-2,2-indole compound with a yield of 86% and a melting point of 190 -192°C. 1 H NMR (400MHz, CDCl 3 )δ8.95(br,1H),8.73(d,J=3.6Hz,1H),7.78(td,J=7.8,1.7Hz,1H),7.71–7.64(m,1H),7.53(...

Embodiment 2

[0045] A kind of unsymmetrical N-pyridyl-2,2-indole compound, its general chemical structure formula is:

[0046]

[0047] The synthetic method of above-mentioned unsymmetrical N-pyridyl-2,2-indole compound, comprises the following steps:

[0048](1) Under an air atmosphere, mix 0.2 mmol of N-pyridyl indole compound, 0.45 mmol of 6-methyl indole, [Cp*Co(CO)I 2 ]0.006mol, AgSbF 6 0.02mmol, HOPiv 0.05mmol, Ag 2 O 0.4mmol, NaOAc 0.22mmol and toluene 3ml were mixed in a reaction tube, and heated in an oil bath at 110°C for 11h;

[0049] Described N-pyridyl indole compound structural formula is:

[0050] (2) After the reaction was completed, the reaction tube was cooled to room temperature, and the reaction mixture was desalted, washed, concentrated, and purified to obtain the target product with a yield of 72% and a melting point of 194-196°C. 1 H NMR (400MHz, CDCl 3 ) δ8.93(br,1H),8.68–8.58(m,1H),7.66(td,J=7.8,1.9Hz,1H),7.59(dd,J=6.3, 2.6Hz,1H),7.45–7.37 (m,1H),7.25(dd...

Embodiment 3

[0052] A kind of unsymmetrical N-pyridyl-2,2-indole compound, its general chemical structure formula is:

[0053]

[0054] The synthetic method of above-mentioned unsymmetrical N-pyridyl-2,2-indole compound, comprises the following steps:

[0055] (1) Under an air atmosphere, mix N-pyridyl indole compound 0.2mmol, 5-chloroindole 0.5mmol, [Cp*Co(CO)I 2 ]0.0056mmol, AgSbF 6 0.022mol, HOPiv 0.044mol, Ag 2 O 0.42mmol, NaOAc 0.2mmol and toluene 2.2ml were mixed in a reaction tube, heated in an oil bath at 110°C for 13h;

[0056] Described N-pyridyl indole compound structural formula is:

[0057] (2) After the reaction was completed, the reaction tube was cooled to room temperature, and the reaction mixture was desalted, washed, concentrated, and purified to obtain the target product with a yield of 82% and a melting point of 180-182°C. 1 H NMR (400MHz, DMSO) δ11.76 (br, 1H), 8.71 (d, J = 3.6Hz, 1H), 8.02 (td, J = 7.7, 1.8Hz, 1H), 7.72 (dd, J = 5.4, 3.2Hz, 1H), 7.58(dd, J=...

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Abstract

The invention discloses an asymmetric N-pyridyl-2,2-diindyl compound and a synthetic method thereof. The synthetic method comprises the following steps of mixing N-pyridyl indole compound, an indole compound, [Cp*Co(CO)I2], AgSbF6, trimethylacetic acid HOPiv, Ag2O, NaOAc and an organic solvent with an air atmosphere in a reaction tube, and performing oil bath reaction to obtain the symmetric N-pyridyl-2,2-diindyl compound. The synthetic method avoids pre-functionalization of an indole substrate in the traditional asymmetric diindyl compound and thus greatly improving the efficiency and the atom economy of reaction; an obtained product is high in yield, narrow in melting point range and high in purity; and in addition, reaction does not need water-free and oxygen-free operation, and operation is simple, rapid and feasible.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to an unsymmetrical N-pyridyl-2,2-indole compound and a synthesis method thereof. Background technique [0002] 2,2-Indole compounds and their derivatives are an important class of organic heterocycles, which have important biological activities and certain medicinal value. [0003] C.A.Merlic et al. (Tetrahedron.2001, 57, 5199) reported an asymmetric 2,2-indole compound, which was mainly constructed through a Pd-catalyzed coupling reaction, as shown in the following formula: [0004] [0005] The main disadvantages of this method are: the selective prefunctionalization of indole substrates is difficult, and the synthesis of 2-iodoindole and 2-indole boronic acid or 2-indole tin-based compounds and zinc compounds is extremely difficult, requiring extremely Severe conditions and multi-step operations. Therefore, it is of great significance to develop a simpl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14
CPCC07D401/14
Inventor 李亭李波柳文敏马勤阁
Owner NANYANG NORMAL UNIV
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