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Method for preparing 3-benzylidene-2-(7'-quinoline)-2,3-dihydro-isoindol-1-one compounds

A ketone compound and benzylidene technology is applied in the field of preparation of pharmaceutical synthesis intermediates, and can solve the problems of low reaction efficiency and many reaction steps, and achieve the effects of convenient post-processing, low equipment requirements and cost saving.

Active Publication Date: 2021-08-17
JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above methods have the disadvantages of many reaction steps and low reaction efficiency.

Method used

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  • Method for preparing 3-benzylidene-2-(7'-quinoline)-2,3-dihydro-isoindol-1-one compounds
  • Method for preparing 3-benzylidene-2-(7'-quinoline)-2,3-dihydro-isoindol-1-one compounds
  • Method for preparing 3-benzylidene-2-(7'-quinoline)-2,3-dihydro-isoindol-1-one compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the preparation of product 4a

[0024]

[0025] At room temperature, add 610mg (5mmol) of benzoic acid 1a, 625mg (6mmol) of styrene 2a and 721mg (5mmol) of 7-aminoquinoline 3a into a 25mL round-bottomed flask, and then add 578mg (0.5mmol) of tetrathree Phenylphosphine palladium, 15 mL of 1,4-dioxane and 1010 mg (10 mmol) of triethylamine were stirred at 100° C. for 8 hours. After the reaction is complete, add 15 mL saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 10 mL each time, combine the organic phases, dry with anhydrous sodium sulfate, evaporate the solvent, and perform 200-300 mesh silica gel column chromatography The pure product of 4a was obtained (1411 mg, 81% yield, pale yellow solid).

[0026] 1 H NMR (400MHz, CDCl 3 )δ8.86(dd, J=4.2,1.7Hz,1H),7.98(dd,J=11.2,4.6Hz,2H),7.89(d,J=7.8Hz,1H),7.69(td,J=7.6 ,1.1Hz, 1H),7.60–7.54(m,2H),7.48(dd,J=7.3,1.4Hz,1H),7.33–7.27(m, 2H),6.81(s,1H),6.67(dd, J=11...

Embodiment 2

[0027] Embodiment 2: the preparation of product 4b

[0028]

[0029] At room temperature, add 783mg (5mmol) of p-chlorobenzoic acid 1b, 625mg (6mmol) of styrene 2a and 721mg (5mmol) of 7-aminoquinoline 3a into a 25mL round bottom flask, and then add 578mg (0.5mmol) Tetrakistriphenylphosphinepalladium, 15mL of 1,4-dioxane and 1010mg (10mmol) of triethylamine were stirred at 100°C for 8 hours. After the reaction is complete, add 15 mL of saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 10 mL each time, combine the organic phases, dry with anhydrous sodium sulfate, evaporate the solvent, and perform 200-300 mesh silica gel column chromatography The pure product of 4b was obtained (1589 mg, 83% yield, pale yellow solid).

[0030] 1 H NMR (400MHz, CDCl 3 )δ8.84(dd, J=4.2,1.7Hz,1H),7.97(dd,J=8.3,1.7Hz,1H),7.92(d,J=8.1Hz,1H),7.87(d,J=1.6 Hz,1H),7.59 (dd,J=8.2,1.4Hz,1H),7.53(dd,J=8.1,1.7Hz,1H),7.48(dd,J=7.4,1.4Hz,1H),7.32–7.28 (m,2H...

Embodiment 3

[0032] Embodiment 3: the preparation of product 4c

[0033]

[0034] At room temperature, 681mg (5mmol) of p-toluic acid 1c, 625mg (6mmol) of styrene 2a and 721mg (5mmol) of 7-aminoquinoline 3a were added to a 25mL round bottom flask, and then 578mg (0.5mmol) of ) tetrakistriphenylphosphinepalladium, 15mL of 1,4-dioxane and 1010mg (10mmol) of triethylamine, stirred at 100°C for 8 hours. After the reaction is complete, add 15 mL of saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 10 mL each time, combine the organic phases, dry with anhydrous sodium sulfate, evaporate the solvent, and perform 200-300 mesh silica gel column chromatography The pure product of 4c was obtained (1667 mg, 92% yield, pale yellow solid).

[0035] 1 H NMR (400MHz, CDCl 3 )δ8.84(dd, J=4.2,1.6Hz,1H),7.96(dd,J=8.3,1.6Hz,1H),7.87(d,J=7.8Hz,1H),7.68(s,1H), 7.57(d, J=8.2Hz, 1H), 7.47(dd, J=7.3, 1.2Hz, 1H), 7.37(d, J=7.2Hz, 1H), 7.31– 7.27(m, 2H), 6.77(s ,1H...

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Abstract

The invention discloses a method for preparing 3-benzylidene-2-(7'-quinoline)-2,3-dihydro-isoindole-1-ketone compounds. The preparation method is: benzoic acid compound, Styrenic compounds and 7-aminoquinolines are in an organic solvent reaction medium, and transition metals are used as catalysts, fully reacted under the promotion of an organic base, and the product is obtained, and the product is processed to obtain 3-benzylidene-2- (7'-quinoline)-2,3-dihydro-isoindol-1-one compound, formula (I) R 1 One of the following: hydrogen, methyl, methoxy; R 2 It is selected from one of the following: hydrocarbon group, aryl group, ether group, ester group; the preparation conditions of the present invention are mild, and the reaction is carried out under normal pressure; the cost is saved, and the requirements for equipment are low; the solvent used has a low boiling point to save energy; post-treatment The method is convenient and meets the requirements of environmental protection, and the obtained product has great industrial application prospects in the fields of chemical industry and material synthesis.

Description

technical field [0001] The invention belongs to the technical field of preparation of pharmaceutical synthesis intermediates, in particular to a palladium-catalyzed preparation of 3-benzylidene-2-(7'-quinoline)-2,3-dihydro-isoindol-1-one compounds Methods. Background technique [0002] 3-benzylidene-2-(7'-quinoline)-2,3-dihydro-isoindol-1-one compounds are an important class of pharmaceutical synthesis intermediates, which have important roles in the synthesis industry and pharmaceutical industry. extensive and important applications. 3-benzylidene-2-(7'-quinoline)-2,3-dihydro-isoindol-1-one compounds exist in the core structure red of many natural organic substances and physiologically active substances, and are used for the treatment of gastric cancer , esophageal cancer and pancreatic cancer have broad medical and biochemical application prospects. At the same time, 3-benzylidene-2-(7'-quinoline)-2,3-dihydro-isoindol-1-one compounds can also be used as chiral auxiliary...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 蔡荣荣熊飞翔
Owner JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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