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

Preparation method of 7-fluoro-2-oxoindoline-4-carboxylic acid

An indoline and oxo technology, applied in the direction of organic chemistry, etc., can solve the problems of large-scale production danger, hazardous waste liquid environment, and high risk coefficient, and achieves easy industrialization amplification, improved safety, and high reaction yield. Effect

Pending Publication Date: 2021-12-17
上海皓鸿生物医药科技有限公司
View PDF7 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The above route uses bromine as a reagent, bromine has strong volatility and strong sensitization, large-scale production is dangerous, and pollutes the environment; using metal zinc reagent, activated metal zinc has strong spontaneous combustion , the risk factor is high in industrial production; the zinc salt produced is difficult to handle, and the waste liquid is harmful to the environment and needs special treatment

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
  • Preparation method of 7-fluoro-2-oxoindoline-4-carboxylic acid
  • Preparation method of 7-fluoro-2-oxoindoline-4-carboxylic acid
  • Preparation method of 7-fluoro-2-oxoindoline-4-carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Add 250ml of ethylene glycol into a 500ml three-necked flask, add 50g (205mmol) of the compound shown in formula (II) and 15.4g (250mmol) of hydrazine hydrate (80%), stir for 30min, control the internal temperature at 55-65°C, and react 2 -6h, the central control raw material disappeared, and the reaction was completed. Cool down to room temperature and filter to obtain 60 g of the crude product represented by formula (III) (the next reaction can be directly carried out without further treatment).

Embodiment 2

[0050] Add 500ml of ethylene glycol into a 500ml three-necked flask, add 60g of the crude product shown in (III) obtained above, add 1.7g (20.5mmol) of sodium acetate, and raise the reaction temperature to 135-145°C, react for 8-16h, and control The reaction is complete. Concentrate under reduced pressure to 1 / 3 of the original volume, cool down to 0-10°C, filter, rinse with 100ml of water, and vacuum-dry to obtain 40g of the compound represented by formula (IV), with a purity of ≥98%.

Embodiment 3

[0052] In the pressure reactor of 500ml, add methanol 300ml, add the compound 30g shown in (IV) obtained above, add triethylamine 27ml, (dppf)PdCl 2 1.55g, replace with CO three times, control the pressure of CO in the reactor to 0.5MPa; control the reaction temperature at 115-125°C, react for 10h, cool down to room temperature, concentrate the solvent, add DMF and DCM, stir for 30min, and filter to obtain formula (V) The compound shown is 23g, with a purity≥98%.

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 provides a preparation method of 7-fluoro-2-oxoindoline-4-carboxylic acid, wherein the method adopts a synthetic route as shown in the specification and specifically comprises the steps: step 1, adding a compound (IV) into a solvent, adding a catalyst and alkali, introducing carbon monoxide gas, and reacting to prepare a compound (V); and step 2, hydrolyzing the compound (V) under the condition of alkali to obtain a compound (I) 7-fluoro-2-oxoindoline-4-carboxylic acid. According to the preparation method provided by the invention, 4-bromo-7-fluoroindoline-2,3-diketone is taken as a raw material, the raw material is easy to obtain, and the related reaction has the characteristics of high safety, high yield, simplicity and convenience in operation, easiness in industrial production and the like.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a method for preparing 7-fluoro-2-oxoindoline-4-carboxylic acid. Background technique [0002] Benzo[b]pyrrole ring derivatives are the most common heterocyclic motifs in natural products The indole family includes many notable representatives such as the essential α-amino acid tryptophan, its spoilage products, the plant growth factor 3-indole Indoleacetic acid (heterologous auxin), neurotransmitter serotonin, pineal hormone melatonin, Rauwolfia alkaloids, reserpine and yohimbine, ranunculus alkaloids, ellipsomycin, strychnium alkaloids, Ning, ergotamine and vinca alkaloids, vincristine. However, many natural plants have very large toxic and side effects. Later, by optimizing the structure of this large class of indole family compounds, their toxicity can be significantly reduced and their efficacy can be improved, and anti-hypertensive, anti-proliferation, anti-virus,...

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): C07D209/34
CPCC07D209/34Y02P20/55
Inventor 彭东杰路化雷苏岭岭何玉林李硕梁杨绍波高强郑保富
Owner 上海皓鸿生物医药科技有限公司
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

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com