Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Benzofuro[2,3-c]pyridine compound and its synthesis method

A benzofuran and synthetic method technology, applied in the field of organic intermediate synthesis, can solve the problems of high cost, harsh reaction conditions, complex process, etc., and achieve the effect of low cost, small environmental impact, and simple process

Inactive Publication Date: 2015-12-09
WUHAN UNIV OF TECH
View PDF4 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned method for synthesizing benzofuro[2,3-c]pyridine compounds has complex steps and harsh reaction conditions, for example, it needs to be carried out under anhydrous and oxygen-free reaction conditions, etc.
Wen et al. used 3-chloropyridine to react with tributyltin chloride at -78°C, and the resulting product reacted with o-iodophenol under the condition of palladium chloride to generate intermediate 2-(3-chloropyridine-4 -yl) phenol, the intermediate forms a ring under the catalysis of tert-butyl sodium to obtain benzofuro[2,3-c]pyridine, and the total yield of the reaction is about 27% (WenSongYueandJieJackLi, AConciseSynthesisofAllFourPossibleBenzo[4,5] furopyridines via Palladium-Mediated Reactions.Org.Lett., Vol.4, No.13, 2002), the reaction is not only demanding on temperature, complex process, and the use of transition metal catalysts, resulting in high cost
In short, the reaction conditions of the currently known synthetic routes are relatively harsh, which greatly limits the industrial application of this type of compound.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Benzofuro[2,3-c]pyridine compound and its synthesis method
  • Benzofuro[2,3-c]pyridine compound and its synthesis method
  • Benzofuro[2,3-c]pyridine compound and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of 3-methyl-1-phenyl-benzofuro[2,3-c]pyridine:

[0030] Weigh 2g of α-bromoacetophenone (10mmol), 1.21g of 4-(2-hydroxyphenyl)-3-buten-2-one (7.5mmol) and 630mg of potassium hydroxide (11.25mmol), add to 40mL of tetrahydrofuran , and the reaction was stirred at 25°C, and the reaction was tracked by thin-layer chromatography. After 1 hour of reaction, 6.1g of ammonium acetate (80mmol) and 80mL of absolute ethanol were added to the system, and the reaction was continued for 3 hours under reflux and stirring, and the reflux temperature was 100°C , the resulting reaction mixture was removed by vacuum distillation to remove the solvent, and then the remaining material was purified with a silica gel column to obtain a light yellow solid product, weighing 1.37g, with a yield of 74%.

[0031] Adopt nuclear magnetic resonance (NMR) method to test the product prepared in this embodiment, such as figure 1 and figure 2 , are respectively the product obtained in this ex...

Embodiment 2

[0036] Synthesis of 3-methyl-1-phenyl-benzofuro[2,3-c]pyridine: the same method as in Example 1 was adopted, except that acetonitrile was used instead of tetrahydrofuran, and the results obtained were basically the same as in Example 1.

Embodiment 3

[0038] Synthesis of 1-(3-bromophenyl)-3-methyl-benzofuro[2,3-c]pyridine:

[0039] Weigh 2.77g 2,3'-dibromoacetophenone (10mmol), 1.21g 4-(2-hydroxyphenyl)-3-buten-2-one (7.5mmol) and 630mg potassium hydroxide (11.25mmol), Add 40mL of tetrahydrofuran, and stir the reaction at 25°C, follow the reaction by thin-layer chromatography, after 2.5h of reaction, add 6.1g of ammonium acetate (80mmol) and 100mL of absolute ethanol to the system, continue to reflux and stir for 3 hours, The reflux temperature was 100°C, and the resulting reaction mixture was distilled under reduced pressure to remove the solvent, and then the remaining substance was purified with a silica gel column to obtain a pale yellow solid product weighing 1.17 g with a yield of 46%.

[0040] Adopt the method identical with embodiment one to test the product prepared in this embodiment, as image 3 and Figure 4 , are respectively the product obtained in this example 1 HNMR spectrum and 13 CNMR spectrum, its 1 ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a benzofuran [2, 3-c] pyridine compound and a synthetic method thereof. The benzofuran [2, 3-c] pyridine compound has a general formula shown in the specification, wherein R1 is phenyl, 3-bromo-phenyl, 4-bromo-phenyl, 4-chloro-phenyl, 4-methoxy-phenyl, 3-methyl-phenyl or 4-methyl-phenyl; R2 is hydrogen or 5-chlorine, 5-bromine, 5-tert-butyl, 3,5-ditert-butyl, 4-methoxy, 5-methoxy, 5-methyl, 3,5-dimethyl and 4,5-dimethyl; R3 is methyl or phenyl, 4-bromo-phenyl, 3-bromo-phenyl, 2-chloro-phenyl, 4-chloro-phenyl, 4-methoxy-phenyl and 4-methyl-phenyl. According to the synthetic method disclosed by the invention, alpha-bromoacetophenone or a derivative thereof as well as 4-(2-hydroxyphenyl)-3-butylene-2-ketone or a derivative thereof are used as reactants, and a one-pot method is adopted to synthesize the benzofuran [2, 3-c] pyridine compound. The synthetic method is simple and convenient in step, mild in condition and high in yield.

Description

technical field [0001] The invention belongs to the technical field of synthesis of organic intermediates, in particular to benzofuro[2,3-c]pyridine compounds and a synthesis method thereof. Background technique [0002] Benzofuro[2,3-c]pyridine organic heterocyclic compounds are widely used in organic synthesis, medicine and other fields, and are important pharmaceutical intermediates. In addition, many molecules with physiological activity also contain such structural units. For example, D.G. Wishka et al. synthesized a benzofuro[2,3-c]pyridine compound (I), which is a central nervous system active drug (WO02 / 100857A1); L.A.Gharat et al. synthesized benzofuro[2,3-c]pyridine compound (II), which is an inhibitor of phosphodiesterase-10 (WO2011 / 132051A2). The above-mentioned method for synthesizing benzofuro[2,3-c]pyridine compounds has complicated steps and harsh reaction conditions, for example, it needs to be carried out under anhydrous and oxygen-free reaction conditio...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/048C07D519/00
CPCC07D491/048C07D519/00
Inventor 郑化胡佳兴张方林徐文刚陈小清李青翠张津甫武博王宝龙
Owner WUHAN UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products