Check patentability & draft patents in minutes with Patsnap Eureka AI!

A Green Synthesis Method of Pharmaceutical Intermediate 5-Bromoindole

A synthesis method and intermediate technology, applied in the field of synthesis of 5-bromoindole, which can solve the problems of high requirements for stirring equipment, small production scale, serious environmental pollution, etc., and achieve low cost, small equipment investment, and high safety Effect

Active Publication Date: 2019-02-19
SINOSTEEL ANSHAN RES INST OF THERMO ENERGY CO LTD
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The reports on the synthesis of 5-bromoindole at home and abroad mainly adopt the process of indole sulfonation and then bromination. This process is high acid and high alkali, the product contains high sulfur, and the environment is seriously polluted.
The reaction process takes a long time, requires high stirring equipment, and the yield is relatively low
The biggest disadvantage of this process is that it is easy to introduce the 7-bromo isomer in the bromination process, which is very dangerous for the pharmaceutical industry
At present, this method is mostly used in China to produce 5-bromoindole, and the production scale is small

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
  • A Green Synthesis Method of Pharmaceutical Intermediate 5-Bromoindole
  • A Green Synthesis Method of Pharmaceutical Intermediate 5-Bromoindole

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0092] A green synthesis method for the pharmaceutical intermediate 5-bromoindole, the adopted technical scheme: ① Indoline is obtained from indole through low-temperature and low-pressure liquid-phase hydrogenation; ② Indoline is reacted with an acylating reagent to synthesize N-acetyl Indoline; ③N-acetyl indoline is cleanly brominated to obtain N-acetyl-5-bromoindoline; ④N-acetyl-5-bromoindoline is deacylated under the action of concentrated hydrochloric acid to obtain 5- Bromoindoline; ⑤5-bromoindoline is oxidatively dehydrogenated to obtain the key pharmaceutical intermediate 5-bromoindoline. The specific operation is as follows:

[0093] (1) Synthesis of indoline

[0094] a) Add 100 g (0.85 mol) of indole, 5 g (10% w.t) of palladium carbon catalyst, and 200 g of xylene into an autoclave and stir evenly to obtain a reaction solution A;

[0095] b) After the autoclave is replaced 8 times with nitrogen and 4 times with hydrogen, the reaction solution A is reacted at 2Mpa o...

example 2

[0119] A green synthesis method for the pharmaceutical intermediate 5-bromoindole, the adopted technical scheme: ① Indoline is obtained from indole through low-temperature and low-pressure liquid-phase hydrogenation; ② Indoline is reacted with an acylating reagent to synthesize N-acetyl Indoline; ③N-acetyl indoline is cleanly brominated to obtain N-acetyl-5-bromoindoline; ④N-acetyl-5-bromoindoline is deacylated under the action of concentrated hydrochloric acid to obtain 5- Bromoindoline; ⑤5-bromoindoline is oxidatively dehydrogenated to obtain the key pharmaceutical intermediate 5-bromoindoline. The specific operation is as follows:

[0120] (1) Synthesis of indoline

[0121] a) 100 g (0.85 mol) of indole, 12 g (10% w.t) of palladium carbon catalyst, and 180 g of toluene were put into an autoclave and stirred evenly to obtain a reaction solution A;

[0122] b) After the autoclave has been replaced by nitrogen 8 times and hydrogen 4 times, the reaction solution A is reacted ...

example 3

[0146] A green synthesis method for the pharmaceutical intermediate 5-bromoindole, the adopted technical scheme: ① Indoline is obtained from indole through low-temperature and low-pressure liquid-phase hydrogenation; ② Indoline is reacted with an acylating reagent to synthesize N-acetyl Indoline; ③N-acetyl indoline is cleanly brominated to obtain N-acetyl-5-bromoindoline; ④N-acetyl-5-bromoindoline is deacylated under the action of concentrated hydrochloric acid to obtain 5- Bromoindoline; ⑤5-bromoindoline is oxidatively dehydrogenated to obtain the key pharmaceutical intermediate 5-bromoindoline. The specific operation is as follows:

[0147] (1) Synthesis of indoline

[0148] a) Add 100 g (0.85 mol) of indole, 10 g (10% w.t) of palladium carbon catalyst, and 150 g of xylene into the autoclave and stir evenly to obtain reaction solution A;

[0149] b) After the autoclave has been replaced by nitrogen 8 times and hydrogen 4 times, the reaction solution A is reacted in hydroge...

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 present invention relates to a kind of green synthesis method of pharmaceutical intermediate 5-bromoindole, comprising the following steps: 1. under the action of metal catalyst, indoline is obtained by hydrogenation of indole in liquid phase at low temperature and low pressure; 2. indoline and acetyl N-acetyl indoline can be generated through the action of chemical reagents; ③N-acetyl-indoline can be cleanly brominated to generate N-acetyl-5-bromoindoline; ④N-acetyl-5-bromoindoline 5-Bromoindoline is obtained by deacylation under acidic conditions; ⑤ 5-Bromoindoline is prepared through oxidative dehydrogenation to prepare the key pharmaceutical intermediate 5-Bromoindole. Compared with the prior art, the beneficial effects of the present invention are: 1) develop a new green synthetic process, compared with the original process, effectively control the brominated isomer of 5-bromoindole products, and ensure that the safety of medical products is higher; 2) Compared with the original acetic anhydride and bromine bromination process, the reaction conditions are mild, the environmental pollution is small, and the cost is low. 3) The equipment investment is small, the process is simple, and the equipment is easy to operate. The corrosion is small, and the process is more suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis technology of 5-bromoindole, in particular to a synthesis method for preparing 5-bromoindole from indole through hydrogenation, acylation, bromination, deacylation and oxidative dehydrogenation. Background technique [0002] 5-Bromoindole, English name 5-Bromoindole, molecular formula C 8 h 6 BrN, with a molecular weight of 196.05, is an important pharmaceutical and chemical intermediate. [0003] Indole compounds widely exist in nature, and many indoles with substituents on the benzene ring have physiological activity. 5-substituted indole compounds are important intermediates and have important applications in the synthesis of medicines and dyes. Melatonin (melatonin, N-acetyl-5-methoxyyuyptamine), also known as melatonin, is mainly produced from 5-methoxyindole, it acts directly on the hypothalamus, and has the functions of promoting sleep, regulating endocrine, enhancing immunity, etc. Various physiological ...

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): C07D209/08
CPCC07D209/08
Inventor 王守凯王海洋赵素娟赵巍马赛勇许浩然金丹陈兴
Owner SINOSTEEL ANSHAN RES INST OF THERMO ENERGY CO LTD
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