Unlock instant, AI-driven research and patent intelligence for your innovation.

Pyrrole formic acid esters compound synthesizing method

A technology of ester compounds and pyrrole formic acid, applied in the direction of organic chemistry, etc., can solve the problems of poor reaction regioselectivity, difficult to obtain substrate, long synthesis route, etc., and achieve the effects of simple operation, wide application range and mild reaction conditions.

Active Publication Date: 2019-01-18
HENAN NORMAL UNIV
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It should be pointed out that although pyrrole carboxylate compounds have important research and application value, the effective methods for the synthesis of such compounds are very limited, and these methods often have the disadvantages of difficult access to substrates, long synthetic routes, and limited reaction areas. Inadequacies such as poor selectivity and cumbersome operation

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
  • Pyrrole formic acid esters compound synthesizing method
  • Pyrrole formic acid esters compound synthesizing method
  • Pyrrole formic acid esters compound synthesizing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022]

[0023] Add 1a (0.5mmol, 81mg), acetonitrile (5mL), anhydrous copper acetate (1mmol, 181mg), iodine (0.5mmol, 127mg) and 4-dimethylaminopyridine (DMAP, 0.5 mmol, 61 mg), vacuumized and filled with oxygen (1 atm), placed in an oil bath at 80°C and stirred for 10 h. Then, 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. Filter, spin dry, and separate through silica gel column (petroleum ether / ethyl acetate=100 / 1) to obtain compound 2a (87mg, 65%). 2a (0.3mmol, 81mg), PdCl 2 (0.03mmol, 5.3mg), copper acetate (0.3mmol, 54mg) and potassium iodide (0.3mmol, 50mg) were placed in a 10mL Shrek tube, evacuated and filled with CO, and then ethanol (3mmol, 175μL) and acetonitrile (3mL) Add it to the system, raise the temperature to 80°C, and react for 12h. The reaction system was post-treated to obtain the target product 3a (45 mg, 70%). The charac...

Embodiment 2

[0025] Add 1a (0.5mmol, 81mg), acetonitrile (5mL), anhydrous copper acetate (0.5mmol, 91mg), iodine element (0.125mmol, 32mg) and DMAP (0.5mmol, 61mg) to a 10mL Shrek tube successively, and draw After inflating oxygen (1 atm) under vacuum, it was placed in an oil bath at 80° C. and stirred for 10 h. Then, 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. Filter, spin dry, and separate through silica gel column (petroleum ether / ethyl acetate=100 / 1) to obtain compound 2a (34 mg, 25%). According to the method of Example 1, 2a can be transformed into 3a.

Embodiment 3

[0027] Add 1a (0.5mmol, 81mg), acetonitrile (5mL), anhydrous copper acetate (0.5mmol, 91mg), iodine element (0.25mmol, 64mg) and DMAP (0.5mmol, 61mg) to a 10mL Shrek tube successively, and draw After inflating oxygen (1 atm) under vacuum, it was placed in an oil bath at 80° C. and stirred for 10 h. Then, 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. Filter, spin dry, and separate through silica gel column (petroleum ether / ethyl acetate=100 / 1) to obtain compound 2a (69 mg, 51%). According to the method of Example 1, 2a can be transformed into 3a.

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 discloses a pyrrole formic acid esters compound synthesizing method and belongs to the technical field of organic synthesis. The synthesizing method comprises the steps: adding N-substituted piperidine 1 into a solvent; performing heating reaction in oxygen to obtain iodo-pyrrole compound 2 under the existence of copper acetate, 4-dimethylamino-pyridine and an additive; mixing the compound 2, palladium salt, an oxidant, an additive and alcohol; performing heating reaction in the CO atmosphere to obtain the pyrrole formic acid esters compound 3. According to the method, the iodo-pyrrole compound is synthesized through a serial of cascade reaction of oxidation ring contraction, decarbonylation, dehydrogenation, beta site iodination, aromatization and the like of N-substituted pyrrole; then the iodo-pyrrole compound generates carbonyl extrusion esterification reaction with CO and alcohol to obtain the pyrrole formic acid esters compound. The pyrrole formic acid esters compound synthesizing method has the advantages of simple raw materials, convenience in operation, mild conditions, wide substrate application range and the like. An economic, practical, green, environment-friendly and novel method is provided for synthesizing the pyrrole formic acid esters compound.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of pyrrole carboxylate compounds. Background technique [0002] Pyrrole is an important nitrogen-containing five-membered heterocyclic ring. This structural unit exists in a variety of natural products (such as chlorophyll, heme, and pigments, etc.) and clinical drugs (such as Lipitor for the treatment and prevention of coronary heart disease, etc.) Among them, it is one of the advantageous structural units in the development of new drugs. Therefore, new synthesis methods of pyrrole compounds are important research contents in the fields of synthetic chemistry, medicinal chemistry and biochemistry. [0003] On the other hand, ester group is one of the most important organic functional groups with diverse reactivity. For example, starting from an ester group, new structural units such as methylene, alcohol, aldehyde, ketone, amide, and ac...

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
IPC IPC(8): C07D207/34
CPCC07D207/34
Inventor 张新迎王芳范学森何艳
Owner HENAN NORMAL UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com