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Synthesis method of dicyano substituted biphenyl compounds

A synthesis method and compound technology are used in the synthesis of dicyano-substituted biphenyl compounds, organic synthesis, and the synthesis of biphenyl compounds, and achieve the effect of good application prospects and industrial production potential.

Active Publication Date: 2015-11-25
中博联(东莞)科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] As mentioned above, although the synthetic methods of multiple biphenyl compounds have been disclosed in the prior art, there are still many serious problems such as how to improve the reaction selectivity and product yield.

Method used

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  • Synthesis method of dicyano substituted biphenyl compounds
  • Synthesis method of dicyano substituted biphenyl compounds
  • Synthesis method of dicyano substituted biphenyl compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] Under a nitrogen atmosphere and room temperature, add 100 mmol of the above formula (I) compound, 150 mmol of the above formula (II) compound, and 3 mmol of catalyst to an appropriate amount of organic solvent (an equal-volume mixture of 1,4-dioxane and PEG-200) (for 1mmolNiCl 2 (PPh 3 ) 2 Mixture with 2mmol CuOTf), 10mmol ligand L1 and 10mmol activator NFSI, warming up to 80°C and stirring at this temperature for 8 hours;

[0034] After the reaction was completed, the reaction mixture was naturally cooled to room temperature, and a mixed solution of ethyl acetate and deionized water with a volume ratio of 1:1 was added thereto, fully oscillated, left to stand for stratification, and the organic phase was separated, and the water phase was used again. Ethyl acetate was extracted 2-3 times, all organic phases were combined, dried with anhydrous sodium sulfate, and distilled under reduced pressure, and the residue was subjected to 200-300 mesh silica gel col...

Embodiment 2

[0037]

[0038] In a nitrogen atmosphere and at room temperature, add 100 mmol of the above formula (I) compound, 170 mmol of the above formula (II) compound, and 5 mmol of catalyst to an appropriate amount of organic solvent (an equal volume mixture of 1,4-dioxane and PEG-200) (1.25mmolNiCl 2 (PPh 3 ) 2 Mixture with 3.75mmol CuOTf), 15mmol ligand L1 and 13mmol activator NFSI, warming up to 90°C and stirring at this temperature for 7 hours;

[0039]After the reaction was completed, the reaction mixture was naturally cooled to room temperature, and a mixed solution of ethyl acetate and deionized water with a volume ratio of 1:1 was added thereto, fully oscillated, left to stand for stratification, and the organic phase was separated, and the water phase was used again. Ethyl acetate was extracted 2-3 times, all organic phases were combined, dried with anhydrous sodium sulfate, and distilled under reduced pressure, and the residue was subjected to 200-300 mesh silica gel co...

Embodiment 3

[0042]

[0043] In a nitrogen atmosphere and at room temperature, add 100 mmol of the above formula (I) compound, 200 mmol of the above formula (II) compound, and 6 mmol of catalyst to an appropriate amount of organic solvent (an equal volume mixture of 1,4-dioxane and PEG-200) (1.8mmolNiCl 2 (PPh 3 ) 2 Mixture with 4.2mmol CuOTf), 20mmol ligand L1 and 16mmol activator NFSI, heated to 100°C and stirred at this temperature for 6 hours;

[0044] After the reaction was completed, the reaction mixture was naturally cooled to room temperature, and a mixed solution of ethyl acetate and deionized water with a volume ratio of 1:1 was added thereto, fully oscillated, left to stand for stratification, and the organic phase was separated, and the water phase was used again. Ethyl acetate was extracted 2-3 times, all organic phases were combined, dried with anhydrous sodium sulfate, and distilled under reduced pressure, and the residue was subjected to 200-300 mesh silica gel column ...

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Abstract

The invention provides a synthesis method of dicyano substituted biphenyl compounds shown in the formula (III) in the specification. The method comprises steps as follows: a compound shown in the formula (I) in the specification, a compound shown in the formula (II) in the specification, a catalyst, ligand and an activating agent are added to an organic solvent under a nitrogen condition at the room temperature, the mixture is heated to 80 DEG C-100 DEG C and stirred to have a reaction for 6-8 hours, the mixture is treated after the reaction ends, and then the compounds shown in the formula (III) in the specification are obtained, wherein R is selected from H, C1-C6 alkoxy, nitryl and cyano group. According to the method, a target product can be prepared at high yield through selection and synergism of the catalyst, the ligand, the activating agent and the organic solvent, and the method has a good application prospect and industrial production potential in the technical field of organic chemical synthesis, especially medical intermediate synthesis.

Description

technical field [0001] The invention relates to a method for synthesizing biphenyl compounds, more particularly to a method for synthesizing dicyano-substituted biphenyl compounds, and belongs to the field of organic synthesis, especially the synthesis of pharmaceutical intermediates. Background technique [0002] Biaryl groups appear in many drug compounds, and they usually play the role of the drug mother nucleus in the molecule, thus attracting extensive research interests of researchers. In addition, biaryl groups often appear in semiconductors, light-emitting devices and liquid crystal materials. [0003] There are several traditional methods for constructing biaryl compounds, such as coupling reaction methods such as Stille, Suzuki, Kumada and Negishi. In recent years, a new strategy has been developed and widely praised, which is the direct C-H activation reaction. [0004] After years of research and summarization, a variety of methods related to the C-H activation...

Claims

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Application Information

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IPC IPC(8): C07C255/51C07C253/30C07C255/54
Inventor 李强
Owner 中博联(东莞)科技有限公司
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