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Composite method for amine compound serving as medicine structuring unit

A synthetic method and compound technology, which is applied in the preparation of organic compounds, chemical instruments and methods, and the preparation of aminohydroxyl compounds, can solve the problems of long reaction steps, low yield, and less research, and achieve good scientific research value.

Inactive Publication Date: 2014-10-15
北京麦康医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In all synthetic methods using aryl boronic acid, it is necessary to use various Cu compounds as catalysts, as well as various catalytic promoters, etc., but there are few studies on catalysts other than Cu, and most of the reaction steps too long, resulting in low yield

Method used

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  • Composite method for amine compound serving as medicine structuring unit
  • Composite method for amine compound serving as medicine structuring unit
  • Composite method for amine compound serving as medicine structuring unit

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] In the reaction vessel, add an appropriate amount but sufficient for the organic solvent DMF required for the reaction, then add the compounds of formula (II) and formula (III) corresponding to Example 1 in Table 1, and then add the nickel complex and the phosphine ligand; Wherein the molar ratio of formula (II) and formula (III) compound is 1:1, the molar ratio of formula (II) and nickel complex is 1:0.04, the molar ratio of nickel complex and phosphine ligand is 1:2; Nitrogen is purged thoroughly, and then nitrogen filling and replacement are continued for 2-3 times until the reaction vessel is completely filled with nitrogen, and heated at 70°C for 14 hours. After the reaction reaches the time, filter while it is hot, then use a rotary evaporator to remove the reaction solvent from the filtrate, and the resulting residue is separated by silica gel column chromatography, and the eluent is a mixed solvent of ethyl acetate and acetone with a volume ratio of 1:1. The elu...

Embodiment 2

[0041] In the reaction vessel, add an appropriate amount but sufficient for the organic solvent DMF required for the reaction, then add the compounds of formula (II) and formula (III) corresponding to Example 2 in Table 1, and then add the nickel complex and the phosphine ligand; Wherein the molar ratio of formula (II) and formula (III) compound is 1:2, the molar ratio of formula (II) and nickel complex is 1:0.07, the molar ratio of nickel complex and phosphine ligand is 1:3; Nitrogen is purged thoroughly, and then nitrogen filling and replacement are continued for 2-3 times until the reaction vessel is completely filled with nitrogen, and the reaction is heated at 90°C for 10 hours. After the reaction reaches the time, filter while it is hot, then use a rotary evaporator to remove the reaction solvent from the filtrate, and the resulting residue is separated by silica gel column chromatography, and the eluent is a mixed solvent of ethyl acetate and acetone with a volume ratio ...

Embodiment 3

[0043] In the reaction vessel, add an appropriate amount but sufficient for the organic solvent DMF required for the reaction, then add the compounds of formula (II) and formula (III) corresponding to Example 3 in Table 1, and then add the nickel complex and the phosphine ligand; Wherein the molar ratio of formula (II) and formula (III) compound is 1:3, the molar ratio of formula (II) and nickel complex is 1:0.1, the molar ratio of nickel complex and phosphine ligand is 1:2; Nitrogen was purged thoroughly, and then nitrogen filling and replacement were continued for 2-3 times until the reaction vessel was completely filled with nitrogen, and the reaction was heated at 110°C for 8 hours. After the reaction reaches the time, filter while it is hot, then use a rotary evaporator to remove the reaction solvent from the filtrate, and the resulting residue is separated by silica gel column chromatography, and the eluent is a mixed solvent of ethyl acetate and acetone with a volume rat...

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Abstract

The invention relates to a composite method for an amine compound. The composite method includes that a specific nickel coordination compound is adopted to serve as a catalyst, a phosphine ligand is utilized, and an amino compound and an organic borate are enabled to react in an organic solution so as to obtain the amine compound. The composite method is good in product yield and simple in aftertreatment and is a brand new composite method with researching and industrial values.

Description

technical field [0001] The invention relates to a synthesis method of a nitrogen-containing compound, in particular to a synthesis method of an amine compound which can be used as a drug building block, and belongs to the field of synthesis of pharmaceutical intermediates. Background technique [0002] Amine compounds are very important compounds that can be used to synthesize many active substances such as drugs, dyes, pesticides, liquid crystal compounds, photosensitive compounds, etc., and play an important role and status in the field of organic chemical synthesis. [0003] So far, people have developed the synthesis of a variety of amine compounds, such as the reduction of nitro groups to amino groups to obtain the corresponding amine compounds, and as more complex amine compounds, people have developed cross-coupling reactions to obtain various Aromatic amine compounds. [0004] In addition, researchers have also developed a synthesis method using boric acid. For exam...

Claims

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Application Information

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IPC IPC(8): C07C209/60C07C211/55C07C211/56C07C213/08C07C217/84
Inventor 庄伟萍
Owner 北京麦康医药有限公司
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