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

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Problems solved by technology

These methods often have disadvantages such as limited substrate scope, especially requiring s

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

Examples

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Example Embodiment

[0016] Example 1 Synthesis of 1-methyl-1,3-dihydroindole-2-one using 1-methylindole as a substrate

[0017] Add 0.4 mL of 1,4-dioxane to the 50 mL reaction tube at room temperature, and then add 2 mL of water, stir and mix well, weigh 1-fluoro-1,2-pheniodohydrin-3-(1H)- The ketone (175mg, 0.66mmol) was added to the reaction tube and stirred for 1 min, then the reaction tube was placed in an oil bath at 140°C, and N-methylindole (78mg, 0.6mmol) was added, and a built-in condenser was added. The reaction was carried out in an oil bath at °C for 5 hours, and the TLC dot panel showed that the reaction of the raw materials was complete. The reaction tube was taken out of the oil bath, cooled to room temperature, and 10 mL saturated sodium bicarbonate was added to quench the reaction, and then extracted with 20 mL ethyl acetate. The organic layers were combined and dried with anhydrous sodium sulfate. The organic layer was concentrated by rotary evaporation and passed through the colum...

Example Embodiment

[0018] Example 2 Synthesis of 1-methyl-1,3-dihydroindole-2-one using 1-methylindole as a substrate

[0019] Add 0.4mL 1,4-dioxane to the 50mL reaction tube at room temperature, then add 2mL of water, stir and mix well, weigh 1-chloro-1,2-pheniodohydrin-3-(1H)-one (187mg , 0.66mmol) was added to the reaction tube and stirred for 1 min, 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 placed in an oil bath at 140°C. After reacting for 5 hours, the TLC dot panel showed that the reaction of the raw materials was complete. The reaction tube was taken out of the oil bath and cooled to room temperature. The reaction was quenched by adding 10 mL of saturated sodium bicarbonate, and then extracted with 20 mL of ethyl acetate. The organic layers were combined with anhydrous Dry with sodium sulfate. The organic layer was concentrated by rotary evaporation and separated by colum...

Example Embodiment

[0020] Example 3 Synthesis of 1-methyl-1,3-indolin-2-one using 1-methylindole as a substrate

[0021] Add 2 mL of tetrahydrofuran to the 50 mL reaction tube at room temperature, and then add 2 mL of water, stir and mix well. Weigh 1-chloro-1,2-pheniodohydrin-3-(1H)-one (187mg, 0.66mmol) into the reaction tube and stir for 1 min, then place the reaction tube in a 40℃ oil bath, and add N- Methylindole (78mg, 0.6mmol), plus a built-in condenser, react for 8 hours in an oil bath at 40°C, TLC dots show that the reaction of the raw materials is complete, take the reaction tube out of the oil bath, cool to room temperature, and add 10 mL The reaction was quenched with saturated sodium bicarbonate, and then extracted with 20 mL of ethyl acetate, and the organic layers were combined and 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 2...

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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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