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Preparation method of N-substituted indolone

A technology of indolinone and di-substitution, which is applied in the field of compound preparation, can solve the problems of weak tolerance of reactive functional groups and harsh reaction conditions, and achieve the effects of not easy to deteriorate, easy to prepare, and mild reaction conditions

Inactive Publication Date: 2020-01-07
XIJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The method of preparing corresponding free radicals using Grignard reagents and organolithium reagents as starting materials, because these free radical precursors are very sensitive to water and oxygen, the reaction conditions are relatively harsh, and the tolerance of reactive functional groups is also weak

Method used

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  • Preparation method of N-substituted indolone
  • Preparation method of N-substituted indolone
  • Preparation method of N-substituted indolone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Add N-methyl-N-phenylacrylamide (36.8mg, 0.21mmol, 1.05eq.), potassium phenylpropyltrifluoroborate (45.2mg, 0.2mmol, 1.0eq.) and and silver oxide (46.0mg, 0.2mmol, 1.0eq.), pumped nitrogen three times, injected 1.0mL toluene and 20μL distilled water into the reaction tube under the nitrogen flow environment, screwed the cap of the reaction tube tightly, and stirred vigorously at 25°C for 10 minutes to stop the reaction. The reaction solution was first filtered with diatomaceous earth to remove the reaction residue, the filter cake was washed three times with ethyl acetate, the filtrates were combined, the solvent was removed by rotary evaporation, and then separated by column chromatography to obtain 52.2 mg of the target white solid with a yield of 89%.

[0036] The mechanism formula of the target product is:

[0037] NMR of the target product ( Figure 1~2 ) and high-resolution mass spectrometry, the results are as follows:

[0038] 1 H NMR (400MHz, CDCl 3 )δ7....

Embodiment 2

[0042] Add N-methyl-N-phenylacrylamide (36.8mg, 0.21mmol, 1.05eq.), potassium 4-fluorophenethyltrifluoroborate (46.0mg, 0.2mmol, 1.0eq. .), and silver oxide (46.0mg, 0.2mmol, 1.0eq.), pump nitrogen three times, inject 1.0mL toluene and 20μL distilled water into the reaction tube under the nitrogen flow environment, tighten the cap of the reaction tube, at 25°C Stir vigorously for 10 minutes to stop the reaction. The reaction solution was first filtered with diatomaceous earth to remove the reaction residue, the filter cake was washed three times with ethyl acetate, the filtrates were combined, the solvent was removed by rotary evaporation, and then separated by column chromatography to obtain 54.7 mg of the target white solid with a yield of 92%.

[0043] The mechanism formula of the target product is:

[0044] NMR of the target product ( Figure 3-4 ) and high-resolution mass spectrometry, the results are as follows:

[0045] 1 H NMR (400MHz, CDCl 3 )δ7.25(d, J=7.7Hz, ...

Embodiment 3

[0049]Add N-methyl-N-phenylacrylamide (36.8mg, 0.21mmol, 1.05eq.), potassium 2-thienylethyltrifluoroborate (43.6mg, 0.2mmol, 1.0eq. .), and silver oxide (46.0mg, 0.2mmol, 1.0eq.), replace the nitrogen gas three times, inject 1.0mL toluene and 20μL distilled water into the reaction tube under the nitrogen flow environment, tighten the cap of the reaction tube, at 25°C Stir vigorously for 10 minutes to stop the reaction. The reaction solution was first filtered with diatomaceous earth to remove the reaction residue, the filter cake was washed three times with ethyl acetate, the filtrates were combined, the solvent was removed by rotary evaporation, and then separated by column chromatography to obtain 49.0 mg of the target white solid with a yield of 86%.

[0050] The mechanism formula of the target product is:

[0051] NMR of the target product ( Figure 5-6 ) and high-resolution mass spectrometry, the results are as follows:

[0052] 1 H NMR (400MHz, CDCl 3 )δ7.26(t, J=...

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Abstract

The invention discloses a preparation method of N-substituted indolone. The preparation method comprises the following steps: mixing an N,N-disubstituted acrylamide derivative, potassium alkyl trifluoroborate and silver oxide, adding toluene and a trace amount of water in a nitrogen environment, sealing the system, violently stirring and reacting the obtained mixture at room temperature to obtaina reaction solution, filtering the reaction solution, removing the solvent, and carrying out column chromatography separation to obtain the target product. The method is quick and efficient in the reaction, and functional groups have good tolerance, and are compatible with halogen, ester groups, hydroxyl groups, cyano groups, amino groups and the like.

Description

technical field [0001] The invention belongs to the technical field of compound preparation, and in particular relates to a preparation method of N-substituted indolinone. Background technique [0002] The unique reactivity of free genes has attracted the attention of chemical chemists, and it has played a very important role in organic synthetic chemistry. What reagent to choose as the free radical precursor and how to convert it into the corresponding free radical conveniently and efficiently has become a research hotspot. [0003] Using Grignard reagents and organolithium reagents as starting materials to prepare corresponding free radicals, because these free radical precursors are very sensitive to water and oxygen, the reaction conditions are relatively harsh and the tolerance of reactive functional groups is also weak. The present invention selects alkyltrifluoroborate potassium salt as the free radical precursor, which can exist stably in the air and has high reacti...

Claims

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Application Information

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IPC IPC(8): C07D209/34C07D409/06
CPCC07D209/34C07D409/06
Inventor 丁思懿任花萍朱敏李俊巍于菲
Owner XIJING UNIV
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