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Method for synthesizing indene (1,2-b) indole-10(5H)-ketone compounds

A technology of ketone compound and synthesis method, which is applied in the field of organic synthesis, can solve problems such as difficult starting materials, low yield, and narrow application range of substrates, and achieve mild reaction conditions, simple operation, and wide application range of substrates. Effect

Active Publication Date: 2017-01-25
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the inden[1,2-b]indol-10(5H)-ones in the literature are catalyzed by palladium-catalyzed intramolecular cross-coupling reaction of 3-(2-halobenzoyl)-indole or palladium-catalyzed Catalyzed intramolecular oxidative coupling reaction of 3-arylformylindole, these methods have the disadvantages of difficult preparation of starting materials, narrow scope of substrate application and low yield, which largely limit The scope of application of this type of synthetic method

Method used

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  • Method for synthesizing indene (1,2-b) indole-10(5H)-ketone compounds
  • Method for synthesizing indene (1,2-b) indole-10(5H)-ketone compounds
  • Method for synthesizing indene (1,2-b) indole-10(5H)-ketone compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012]

[0013] In a 15mL schlenk reaction tube, add N-methylindole 1a (0.4mmol, 114mg), palladium acetate (4.5mg, 0.02mmol), n-butylbis(1-adamantyl)phosphine (BuPAd) 2 ) (21.5mg, 0.06mmol), DABCO (134.6mg, 1.2mmol) and dimethyl sulfoxide (1.5mL), vacuum-filled with CO (1atm) three times, then heated and stirred at 120°C for 12h. After the reaction was completed, a saturated ammonium chloride solution was added to the reaction tube to quench the reaction, extracted with dichloromethane, the organic phase was washed with deionized water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=3 / 1) to obtain red solid 5-methylinden[1,2-b]indole-10(5H)-one 2a (84mg, 90%). The characterization data of this compound are as follows: 1 H NMR (CDCl 3 ,400MHz)δ3.84(s,3H),7.13-7.24(m,6H),7.39(d,J=6.8Hz,1H),7.75(d,J=7.6Hz,1H); 13 C NMR (CDCl 3 ,100MHz)δ31.6,110.5,114.9,...

Embodiment 2

[0015]

[0016] According to the method described in Example 1, indole 1b (0.4mmol, 120mg), palladium acetate (4.5mg, 0.02mmol), n-butylbis(1-adamantyl)phosphine were added successively in a 15mL schlenk reaction tube (BuPAd 2 ) (21.5mg, 0.06mmol), DABCO (134.6mg, 1.2mmol) and dimethyl sulfoxide (1.5mL), vacuum-filled with CO (1atm) three times, then heated and stirred at 120°C for 12h. After the reaction was completed, a saturated ammonium chloride solution was added to the reaction tube to quench the reaction, extracted with dichloromethane, the organic phase was washed with deionized water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=3 / 1) to obtain red solid 5,7-dimethylinden[1,2-b]indol-10(5H)-one 2b (88 mg, 89%). The characterization data of this compound are as follows: 1 H NMR (CDCl 3 ,400MHz)δ2.71(s,3H),3.67(s,3H),6.88-6.91(m,2H),7.00-7.15(...

Embodiment 3

[0018]

[0019] According to the method described in Example 1, indole 1c (0.4mmol, 120mg), palladium acetate (4.5mg, 0.02mmol), n-butylbis(1-adamantyl)phosphine were successively added into a 15mL schlenk reaction tube (BuPAd 2 ) (21.5mg, 0.06mmol), DABCO (134.6mg, 1.2mmol) and dimethyl sulfoxide (1.5mL), vacuum-filled with CO (1atm) three times, then heated and stirred at 120°C for 12h. After the reaction was completed, a saturated ammonium chloride solution was added to the reaction tube to quench the reaction, extracted with dichloromethane, the organic phase was washed with deionized water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=3 / 1) to obtain red solid 5,9-dimethylinden[1,2-b]indol-10(5H)-one 2c (94 mg, 95%). The characterization data of this compound are as follows: 1 H NMR (CDCl 3 ,400MHz)δ2.39(s,3H),3.72(s,3H),6.89(s,1H),6.97(d,J=8.0H...

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Abstract

The invention discloses a method for synthesizing indene (1,2-b) indole-10(5H)-ketone compounds. The technical scheme includes: -2-(2-bromiine aryl)-1H-indole derivatives and CO (carbon monoxide) are replaced by N- to serve as an original raw material, palladium acetate serves as a catalyst, DABCO serves as alkali, N-butyl2 (1-adamantyl) phosphine as ligand, dimethyl sulfoxide or N-methyl pyrrolidone serves as a solution, and the target material of the indene (1,2-b) indole-10(5H)-ketone compounds is obtained by heating and stirring to perform reaction in a reactor vessel at the temperature of 120DEG C. The method has the advantages of moderate reaction conditions, easiness in preparation of the original raw materials, wide range of application of zymolyte, simpleness in operation and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of inden[1,2-b]indole-10(5H)-one compounds. Background technique [0002] Indenoindolinone structural units widely exist in natural alkaloids and synthetic drugs, and have attracted a lot of attention from organic and pharmacologists in recent years. Among them, inden[1,2-b]indol-10(5H)-one compounds can not only be used as inhibitors of protein kinase CK2, but also as efficient ligands of melatonin MT3. Most of the inden[1,2-b]indol-10(5H)-ones in the literature are catalyzed by palladium-catalyzed intramolecular cross-coupling reaction of 3-(2-halobenzoyl)-indole or palladium-catalyzed Catalyzed intramolecular oxidative coupling reaction of 3-arylformylindole, these methods have the disadvantages of difficult preparation of starting materials, narrow scope of substrate application and low yield, which largely limit The scope of applica...

Claims

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Application Information

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IPC IPC(8): C07D209/94
CPCC07D209/94
Inventor 郭胜海王芳陶丽范学森
Owner HENAN NORMAL UNIV