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A kind of unsymmetrical n-pyridyl-2,2-diindole compound and its synthesis method

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

Inactive Publication Date: 2021-02-12
NANYANG NORMAL UNIV
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  • 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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  • A kind of unsymmetrical n-pyridyl-2,2-diindole compound and its synthesis method
  • A kind of unsymmetrical n-pyridyl-2,2-diindole compound and its synthesis method
  • A kind of unsymmetrical n-pyridyl-2,2-diindole compound and its synthesis method

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Embodiment 1

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

[0036]

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

[0038] (1) Under an air atmosphere, 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-diindole 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),7.5...

Embodiment 2

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

[0046]

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

[0048] (1) Under an air atmosphere, 0.2 mmol of N-pyridyl indole compound, 0.45 mmol of 6-methyl indole, [Cp*Co(CO)I2 ]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, 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,J=6.7,...

Embodiment 3

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

[0053]

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

[0055] (1) Under an air atmosphere, mix 0.2mmol of N-pyridylindole compound, 0.5mmol of 5-chloroindole, [Cp*Co(CO)I 2 ]0.0056mmol, AgSbF 6 0.022mol, HOPiv 0.044mol, Ag 2 O0.42mmol, 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), 7.5...

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Abstract

The invention discloses an unsymmetrical N-pyridyl-2,2-indole compound and a synthesis method thereof. In an air atmosphere, an N-pyridyl indole compound, an indole compound, [Cp*Co(CO ) I 2 ], AgSbF 6 , pivalic acid HOPiv, Ag 2 O, NaOAc and an organic solvent are mixed in a reaction tube and reacted in an oil bath. The invention avoids the pre-functionalization of the indole substrate in the traditional asymmetric indole compound synthesis method, thereby greatly improving the efficiency and atom economy of the reaction, and the obtained product has high yield, narrow melting point range and high purity. Moreover, the reaction does not require anhydrous and oxygen-free operation, and the operation is simple 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-diindole compound and a synthesis method thereof. Background technique [0002] 2,2-Diindole compounds and their derivatives are an important class of organic heterocyclic rings, which have important biological activities and certain medicinal value. [0003] C.A.Merlic et al. (Tetrahedron.2001, 57, 5199) reported an asymmetric 2,2-diindole compound, which was mainly constructed by 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 ...

Claims

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Application Information

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Patent Type & Authority Patents(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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