2-pyridyl benzimidazole palladium copper heteronuclear compound and its preparation method and application

A technology for pyridyl benzimidazoles and compounds is applied in the field of organic synthesis and achieves the effects of high yield, wide range of reaction substrates and mild catalytic reaction conditions

Inactive Publication Date: 2017-02-22
LUOYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Up to now, there is no report on the synthesis of 2-pyridylbenzimidazole palladium copper heteronuclear compound and its use as a bimetallic catalyst to catalyze the three-component reaction to synthesize 2-pyridylquinoline derivatives

Method used

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  • 2-pyridyl benzimidazole palladium copper heteronuclear compound and its preparation method and application
  • 2-pyridyl benzimidazole palladium copper heteronuclear compound and its preparation method and application
  • 2-pyridyl benzimidazole palladium copper heteronuclear compound and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Example 1: Preparation of 2-pyridylbenzimidazole palladium copper heteronuclear compound (1)

[0034] Add 2-pyridylbenzimidazolium copper bisphosphine compound A (1 mmol), Li 2 PdCl 4 (1 mmol), sodium acetate (1 mmol), 10 ml of anhydrous methanol, temperature 10 ° C, stirring the reaction solution for 12 hours and then filtering. After the obtained solid was dried, it was added to a 10ml flask, and then triphenylphosphine (1 mmol) and 5ml of dichloromethane were added in sequence. After stirring the reaction solution at 20°C for 1 hour, the solvent was distilled off, and dichloromethane and petroleum ether were used to Recrystallized from a mixed solvent to obtain product 1 with a yield of 86%. The obtained product was subjected to nuclear magnetic resonance analysis, and the data were as follows: 1H NMR: δ= 8.71 (d, 1H), 7.93 (d, 1H), 7.81 (d, 2H), 7.57-7.63 (m, 21H), 7.26-7.35 ( m, 17H), 1.83 (t, 4H).

[0035] The structural formula of the 2-pyridylbenzimidazole c...

Embodiment 2

[0037] Example 2: Preparation of 2-pyridylbenzimidazole palladium copper heteronuclear compound (3):

[0038] Add 2-pyridylbenzimidazolium copper bisphosphine compound B (1 mmol), Li 2 PdBr 4 (1.2mmol), sodium acetate (1.1 mmol), 12ml of anhydrous methanol, temperature 20°C, stirring the reaction solution for 20h and then filtering. After drying the obtained solid, add it to a 10ml flask, then add triphenylphosphine (1.2 mmol) and 5ml dichloromethane in sequence, stir the reaction solution at 30°C for 3h, distill off the solvent, and use dichloromethane and petroleum ether Recrystallized from a mixed solvent to obtain product 3 with a yield of 88%. The obtained product was subjected to nuclear magnetic resonance analysis, and the data were as follows: 1H NMR: δ= 8.70 (d, 1H), 7.91 (d, 1H), 7.78 (d, 2H), 7.53-7.61 (m, 21H), 7.24-7.33 ( m, 16H), 2.48 (s, 3H), 1.81 (t, 4H).

[0039] The structural formula of the 2-pyridylbenzimidazolium bisphosphine compound B is as follows: ...

Embodiment 3

[0041] Example 3: Preparation of 2-pyridylbenzimidazole palladium copper heteronuclear compound (6):

[0042] Add 2-pyridylbenzimidazolium bisphosphine compound C (1 mmol), Li 2 PdCl 4 (1.5 mmol), sodium acetate (1.5 mmol), 15 ml of anhydrous methanol, temperature 30 ° C, stirring the reaction solution for 30 h and then filtering. After drying the obtained solid, add it to a 10ml flask, then add trimethylphosphine (1.3 mmol) and 5ml acetone in sequence, stir the reaction solution at 15°C for 6h, distill off the solvent, and use a mixture of dichloromethane and petroleum ether Solvent recrystallization gave product 6 with a yield of 85%. The obtained product was subjected to nuclear magnetic resonance analysis, and the data were as follows: 1H NMR: δ= 8.75 (d, 1H), 7.87 (d, 1H), 7.73 (d, 2H), 7.50-7.59 (m, 12H), 7.20-7.34 ( m, 8H), 3.85 (s, 3H), 1.80 (t, 4H), 0.98(s, 9H).

[0043] The structural formula of the 2-pyridylbenzimidazole cuprous bisphosphine compound C is as fol...

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Abstract

The invention relates to a 2-pyridyl benzimidazole palladium copper heteronuclear compound, the general formula of which is shown as the specification. Specifically, X is Cl<->, Br<-> or I<->; L is a tertiary phosphine ligand; P is a diphosphine ligand; R and R1 can be -H, -CH3, -C2H5 or -OCH3; and R is at any position of aromatic ring 7-10, and R1 is at any position of pyridine ring 3-5. The compound can serve as a bimetallic catalyst to catalyze the three-component reaction of 2-acetylpyridine, 2-amino halogenated benzylalcohol and arylboronic acid so as to synthesize a 2-pyridyl quinoline derivative.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a 2-pyridyl benzimidazole palladium copper heteronuclear compound and a preparation method and application thereof. Background technique [0002] Metal-organic chemistry is an interdisciplinary subject between organic chemistry and inorganic chemistry. Metal-organic compounds used as reagents or catalysts have made great achievements in organic synthetic chemistry. Now the chemical reaction catalyzed by metal organic compounds has become the cornerstone of major chemical industry, pharmaceutical industry and fine chemical industry. Among the many transition metal organic compounds, palladium compounds occupy an important position in organic chemistry and industrial catalysis due to their excellent catalytic properties, and have always been one of the frontiers of chemists' research. Up to now, more and more new palladium compounds have been synthesized to meet the requ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F19/00B01J31/24C07D401/04C07D401/14C07D405/14C07D409/14
Inventor 李红梅徐晨王志强娄新华付维军
Owner LUOYANG NORMAL UNIV
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