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A kind of synthetic method of pharmaceutical intermediate 2-aroyl indole derivative

A technology for the synthesis of aroyl indole derivatives and synthesis methods, which is applied in the synthesis of pharmaceutical intermediates 2-aroyl indole derivatives and in the field of synthesis of indole compounds, and can solve the problem of insufficient raw material sources, low material utilization, and Low product yield and other problems, to achieve the effect of ideal yield, broad market prospects, and convenient process

Active Publication Date: 2018-07-17
江西远邦药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these existing methods often have many problems, such as insufficient raw material sources, high production costs, low material utilization, low product yields, etc.

Method used

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  • A kind of synthetic method of pharmaceutical intermediate 2-aroyl indole derivative
  • A kind of synthetic method of pharmaceutical intermediate 2-aroyl indole derivative
  • A kind of synthetic method of pharmaceutical intermediate 2-aroyl indole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] In an appropriate amount of organic solvent (a mixture of 1-cyanopropyl-3-methylimidazolium tetrafluoroborate and ethylene glycol at a mass ratio of 1:4), add 100 mmol of the compound of the above formula (I), 100 mmol of the above formula ( II) compound, 15mmol catalyst (a mixture of 3.75mmol 1-diphenylphosphino-1'-(di-tert-butylphosphino)ferrocene and 11.25mmol tin iodide), 150mmol base 1,5,7- Triazabicyclo[4.4.0]dec-5-ene (TBD) and 16 mmol auxiliary cerium trifluoromethanesulfonate (Ce(OTf) 3 ), then warming up to 80°C, and stirring and reacting at this temperature for 12 hours;

[0036] After the reaction, add deionized water to the reaction system to fully shake and wash, then extract 2-3 times with chloroform, combine the organic phases, and wash again with saturated brine, dry over anhydrous magnesium sulfate, concentrate under reduced pressure, and filter the residue over 300-400 mesh silica gel column chromatography, eluting with a mixture of aceto...

Embodiment 2

[0039]

[0040]In an appropriate amount of organic solvent (a mixture of 1-cyanopropyl-3-methylimidazolium tetrafluoroborate and ethylene glycol at a mass ratio of 1:4), add 100 mmol of the compound of the above formula (I), 200 mmol of the above formula ( II) compound, 5mmol catalyst (a mixture of 1mmol 1-diphenylphosphino-1'-(di-tert-butylphosphino)ferrocene and 4mmol tin iodide), 250mmol base 1,5,7-triazol Heterobicyclo[4.4.0]dec-5-ene (TBD) and 10 mmol auxiliary cerium trifluoromethanesulfonate (Ce(OTf) 3 ), then warming up to 100°C, and stirring and reacting at this temperature for 8 hours;

[0041] After the reaction is over, add deionized water to the reaction system to fully shake and wash, then extract 2-3 times with chloroform, combine the organic phases, and wash again with saturated brine, dry over anhydrous magnesium sulfate, concentrate under reduced pressure, and filter the residue over 300-400 mesh silica gel column chromatography, eluting with a mixture of...

Embodiment 3

[0044]

[0045] In an appropriate amount of organic solvent (a mixture of 1-cyanopropyl-3-methylimidazolium tetrafluoroborate and ethylene glycol at a mass ratio of 1:4), add 100 mmol of the compound of the above formula (I), 150 mmol of the above formula ( II) compound, 10mmol catalyst (a mixture of 2.2mmol 1-diphenylphosphino-1'-(di-tert-butylphosphino) ferrocene and 7.8mmol tin iodide), 200mmol base 1,5,7-tri Azabicyclo[4.4.0]dec-5-ene (TBD) and 13 mmol auxiliary cerium trifluoromethanesulfonate (Ce(OTf) 3 ), then warming up to 90°C, and stirring and reacting at this temperature for 10 hours;

[0046] After the reaction is over, add deionized water to the reaction system to fully shake and wash, then extract 2-3 times with chloroform, combine the organic phases, and wash again with saturated brine, dry over anhydrous magnesium sulfate, concentrate under reduced pressure, and filter the residue over 300-400 mesh silica gel column chromatography, eluting with a mixture of...

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Abstract

The invention relates to a synthetic method for a 2-aroylindole derivative capable of being used as a medical intermediate and shown as the formula (III). The method comprises the following steps: in an organic solvent, enabling a compound shown as the formula (I) and a compound shown as the formula (II) to react in the presence of a catalyst, an alkali and an auxiliary agent; after the reaction is finished, treating to obtain the compound shown as the formula (III), wherein R1 and R2 are independently selected from H, C1-C6 alkyl, nitryl or halogen respectively. According to the method provided by the invention, the simple reaction raw materials are adopted and comprehensive compounding and cooperation of the catalyst, the alkali, the auxiliary agent and the organic solvent are carried out, so that the yield of the target product is high; the synthetic method has the advantages of simple process, ideal yield and low cost and shows a wide market prospect.

Description

technical field [0001] The invention relates to a method for synthesizing indole compounds, more particularly to a method for synthesizing a drug intermediate 2-aroyl indole derivative, and belongs to the field of organic synthesis. Background technique [0002] 2-Aroyl indoles are ubiquitous structural units in natural products and pharmaceutical compounds, which often exhibit diverse biological activities. For example, receptor tyrosine kinase inhibitors, histone deacetylase inhibitors, etc. can be designed and constructed. [0003] Despite having such important and extensive biological value, there are few reports on the synthesis process of 2-aroyl indole compounds. Therefore, the development of efficient synthetic methods for 2-aroyl indole compounds is one of the key issues faced by scientific researchers. [0004] In recent years, some synthetic methods related to 2-aroyl indole compounds have emerged in the prior art, such as: [0005] A Cu( OTf) 2 The preparati...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/12
CPCC07D209/12
Inventor 不公告发明人
Owner 江西远邦药业有限公司