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Method for directly synthesizing substituted 2-indolone by substituted indole under neutral condition

A neutral-condition, indolinone technology is applied in the field of directly synthesizing substituted 2-indolinone under neutral conditions for substituted indole, and achieves the effects of high yield, simple operation and high-efficiency preparation method

Active Publication Date: 2018-06-08
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods often have disadvantages such as limited substrate scope, especially requiring substituents at the 3- and 5-positions, which would otherwise place halogens on these positions

Method used

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  • Method for directly synthesizing substituted 2-indolone by substituted indole under neutral condition

Examples

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Effect test

Embodiment 1

[0016] Example 1 Synthesis of 1-methyl-1,3-dihydroindolin-2-one with 1-methylindole as substrate

[0017] Add 0.4mL of 1,4-dioxane to a 50mL reaction tube at room temperature, then add 2mL of water, stir and mix well, weigh 1-fluoro-1,2-phenyliodohydrin-3-(1H)- Ketone (175mg, 0.66mmol) was added to the reaction tube and stirred for 1min, then the reaction tube was placed in an oil bath at 140°C, N-methylindole (78mg, 0.6mmol) was added, and a built-in condenser was added, and the reaction tube was heated at 140°C The reaction was carried out in an oil bath at ℃ for 5 hours, and the TLC spot plate showed that the reaction of the raw materials was complete. Take the reaction tube out of the oil bath, cool to room temperature, add 10 mL of saturated sodium bicarbonate to quench the reaction, then extract with 20 mL of ethyl acetate, combine the organic layers and dry them with anhydrous sodium sulfate. Analysis and separation gave 79 mg of yellow solid N-methyl-2 indolinone with...

Embodiment 2

[0018] Example 2 Synthesis of 1-methyl-1,3-dihydroindolin-2-one with 1-methylindole as substrate

[0019] Add 0.4mL of 1,4-dioxane to a 50mL reaction tube at room temperature, then add 2mL of water, stir and mix well, weigh 1-chloro-1,2-phenyliodohydrin-3-(1H)-one (187mg , 0.66mmol) was added to the reaction tube and stirred for 1min, then the reaction tube was placed in a 140°C oil bath, N-methylindole (78mg, 0.6mmol) was added, and a built-in condenser was added, and the reaction tube was placed in a 140°C oil bath Reacted in medium for 5 hours, TLC spot plate showed that the raw materials had reacted completely, took the reaction tube out of the oil bath, cooled to room temperature, added 10mL saturated sodium bicarbonate to quench the reaction, then extracted with 20mL ethyl acetate, combined the organic layers with anhydrous Na2SO4 dried. The organic layer was concentrated by rotary evaporation, and separated by column chromatography to obtain 55 mg of yellow solid N-met...

Embodiment 3

[0020] Example 3 Synthesis of 1-methyl-1,3-dihydroindolin-2-one with 1-methylindole as substrate

[0021] Add 2 mL of tetrahydrofuran to a 50 mL reaction tube at room temperature, then add 2 mL of water, and stir to mix. Weigh 1-chloro-1,2-phenyliodohydrin-3-(1H)-one (187mg, 0.66mmol) into the reaction tube and stir for 1min, then place the reaction tube in an oil bath at 40°C, add N- Methylindole (78mg, 0.6mmol) was reacted in an oil bath at 40°C for 8 hours with a built-in condenser. TLC spotting showed that the reaction of the raw materials was complete. Take the reaction tube out of the oil bath, cool to room temperature, and add 10mL The reaction was quenched with saturated sodium bicarbonate, extracted with 20 mL of ethyl acetate, and the combined organic layers were dried over anhydrous sodium sulfate. The organic layer was concentrated by rotary evaporation, and separated by column chromatography to obtain 24 mg of yellow solid N-methyl-2-indolinone with a yield of 27...

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Abstract

The invention relates to a method for directly synthesizing substituted 2-indolone by substituted indole under the neutral condition. The method comprises the following steps of sequentially adding organic solvents and water according to the proportion of 1:1-1:20 at the room temperature; then, adding high-iodine reagents; raising the temperature to 40 to 160 DEG C; then, adding indole; performingreaction for 1 to 8 hours to obtain the substituted 2-indolone compounds. The method has the main innovation point that under the neutral condition, substituted 2-indolone is directly synthesized through indole oxidization; the use of strong acid reagents is avoided. The method has the advantages that the raw materials are cheap and can be easily obtained; the operation is simple and convenient;the substrate universality is high; the reaction yield is high, and the like.

Description

technical field [0001] The invention relates to a method for directly synthesizing substituted 2-indolinones with substituted indoles under neutral conditions. Background technique [0002] Substituted 2-indolinone is a special aromatic heterocyclic structure, and it is also the core to construct many biologically active alkaloids and medicinally active compounds. Among them, substituted substituted 2-indolinone compounds play a very important role. These compounds have good biological activities, such as anti-inflammatory, antibacterial, and antitumor, and are widely used in the fields of medicine and pesticides. In 1996, the early Parkinson's disease treatment drug ropinirole hydrochloride (Requip) developed by the British Smith Kline-Beecham Company is a potent and selective non-ergot alkaloid dopamine D2-receptor agonist, which can directly stimulate striatum Body dopamine receptors, thereby improving bradykinesia, stiffness, tremor and depression, improving patients' d...

Claims

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Application Information

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IPC IPC(8): C07D209/34A61P29/00A61P31/04A61P35/00A01P1/00
CPCC07D209/34
Inventor 姜昕鹏郑聪雷丽君林凯俞传明苏为科
Owner ZHEJIANG UNIV OF TECH
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