Synthesis method of (3-cyclopropylpyridin-2-yl) methylamine

A technology for the synthesis of cyclopropylpyridine and its method, which is applied in the field of synthesis of (3-cyclopropylpyridin-2-yl)methylamine, achieving the effects of high yield, simple operation and short route

Inactive Publication Date: 2020-07-17
阿里生物新材料(常州)有限公司
View PDF1 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis method of (3-cyclopropylpyridin-2-yl) methylamine is rarely reported in the literature

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
  • Synthesis method of (3-cyclopropylpyridin-2-yl) methylamine
  • Synthesis method of (3-cyclopropylpyridin-2-yl) methylamine
  • Synthesis method of (3-cyclopropylpyridin-2-yl) methylamine

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0025] A kind of synthetic method of (3-cyclopropylpyridin-2-yl) methylamine, this synthetic method comprises the steps:

[0026] (1) Dissolving 3-bromopyridine in an organic solvent, adding an oxidant at -10 to 0°C, and performing an oxidation reaction to obtain Compound A;

[0027] (2) Dissolve compound A in acetonitrile, under nitrogen protection, and carry out cyanation reaction with trimethylsilyl cyanide and triethylamine at 70-80°C to obtain compound B;

[0028] (3) Dissolve compound B in toluene, sequentially add cyclopropylboronic acid, potassium phosphate, tricyclohexylphosphine, water, and palladium acetate under nitrogen protection, and carry out coupling reaction at 100-105°C to obtain compound C;

[0029] (4) Dissolve compound C in methanol, add Raney nickel and ammonia water in a hydrogen atmosphere, and perform a reduction reaction to obtain (3-cyclopropylpyridin-2-yl)methylamine.

[0030] In the step (1), the organic solvent is dichloromethane, the oxidizing ...

Embodiment

[0035] Compound A: Synthesis of 3-bromopyridine monoxide

[0036]

[0037] Dissolve 20g of 3-bromopyridine in 300mL of organic solvent dichloromethane, add 48g of oxidant m-chloroperoxybenzoic acid at -10~0°C, stir, and carry out oxidation reaction for 3.5h, then add saturated carbonic acid under ice bath Sodium hydrogen aqueous solution 120mL, stirred for 30min, dichloromethane and methanol were mixed at a volume ratio of 8:1, extracted 7 times, and the organic phase was dried with anhydrous sodium sulfate, concentrated, and column chromatographed to obtain 20g of 3-bromo Pyridine monoxide, the yield is 90.8%.

[0038] Compound B: Synthesis of 3-bromopyridine-2-carbonitrile

[0039]

[0040] Dissolve 20 g of the prepared 3-bromopyridine monoxide in 300 mL of acetonitrile, under nitrogen protection, and 35 g of trimethylsilyl cyanide and 24 g of triethylamine at 70 to 80 ° C, reflux overnight to carry out cyanation reaction, After cooling, the reaction solution was pou...

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 belongs to the technical field of medical intermediates, and particularly relates to a synthesis method of (3-cyclopropylpyridin-2-yl) methylamine. The synthesis method of the (3-cyclopropylpyridin-2-yl) methylamine is provided for the first time, a synthesis route is provided for the synthesis method of the (3-cyclopropylpyridin-2-yl) methylamine, the synthesis method of the (3-cyclopropylpyridin-2-yl) methylamine is short in route, reasonable in design, easy to operate and easy to control, and meanwhile the yield of the obtained product is high.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical intermediates, in particular to a method for synthesizing (3-cyclopropylpyridin-2-yl)methylamine. Background technique [0002] The compound (3-cyclopropylpyridin-2-yl)methanamine and related derivatives are widely used in medicinal chemistry and organic synthesis. At present, the synthetic method of (3-cyclopropylpyridin-2-yl)methanamine is rarely reported in the literature. Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, suitable for overall yield, and suitable for industrial production. Contents of the invention [0003] Technical problem to be solved by the present invention: Aiming at the problems mentioned above, a method for synthesizing (3-cyclopropylpyridin-2-yl)methylamine is provided. [0004] In order to solve the problems of the technologies described above, the present invention a...

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 Applications(China)
IPC IPC(8): C07D213/38
CPCC07D213/38
Inventor 史建云许义波戴红升
Owner 阿里生物新材料(常州)有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap