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Method for preparing N-arylsulfonamide from indoline and arylsulfonamide

A technology of arylsulfonamide and indoline, which is applied in the field of C-H bond activation, can solve the problems of restricting large-scale use and generating a large amount of waste, and achieves the effects of short reaction time, easy-to-obtain catalyst and wide applicability

Active Publication Date: 2019-09-10
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

(See: Kim, T.; McCarver, S.; Lee, C.; MacMillan, D. Angew. Chem. Int. Ed. 2018, 57, 3488-3492.) However, the use of halogenated Pre-functionalized reagents such as hydrocarbons or aryl boronic acids, and after the reaction is completed, a large amount of waste will be generated, which undoubtedly limits the large-scale use of the above method

Method used

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  • Method for preparing N-arylsulfonamide from indoline and arylsulfonamide
  • Method for preparing N-arylsulfonamide from indoline and arylsulfonamide
  • Method for preparing N-arylsulfonamide from indoline and arylsulfonamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Preparation of N-(1-acetylindolin-7-yl)-4-methylbenzenesulfonamide N-(1-acetylindolin-7-yl)-4-methylbenzenesulfonamide

[0023]

[0024] In the dried Schlenk tube, the raw materials indoline (0.15 mmol, 24.1 mg), p-toluenesulfonamide (0.3 mmol, 51.1 mg), iodobenzene acetate (0.15 mmol, 48.3 mg), pentamethyl Cyclopentadienyl rhodium dichloride (5 mmol%, 4.6 mg), additives, silver trifluoromethanesulfonate (20 mmol%, 7.7 mg), silver acetate (20% mmol, 5.1 mg), acetic acid (0.45 mmol, 27 mg) 1.5 mL of 1,2-dichloroethane, and put the above-mentioned Schlenk tube at 100 o In a C oil bath, stir for about 16 h. The reaction was terminated, and the reaction solution was easily quenched with 2 mL of saturated ammonium chloride, and extracted several times with ethyl acetate (4 mL × 5), the organic phases were combined, and the solvent was removed on a rotary evaporator. Finally, separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether...

Embodiment 2

[0026] Example 2: Preparation of N-(1-acetyl-2-methylindolin-7-yl)-4-methylbenzenesulfonamide N-(1-acetyl-2-methylindolin-7-yl)-4 -methylbenzenesulfonamide

[0027]

[0028] In the dried Schlenk tube, add the raw materials indoline (0.15 mmol, 26.2 mg), p-toluenesulfonamide (0.3 mmol, 51.1 mg), iodobenzene acetate (0.15 mmol, 48.3 mg), pentamethyl Cyclopentadienyl rhodium dichloride (5% mmol, 4.6 mg), additives, silver trifluoromethanesulfonate (20% mmol, 7.7 mg), silver acetate (20% mmol, 5.1 mg), acetic acid (0.45 mmol, 27 mg) 1.5 mL of 1,2-dichloroethane, and put the above-mentioned Schlenk tube at 100 o In a C oil bath, stir for about 16 h. The reaction was terminated, and the reaction solution was easily quenched with 2 mL of saturated ammonium chloride, and extracted several times with ethyl acetate (4 mL × 5), the organic phases were combined, and the solvent was removed on a rotary evaporator. Finally, it was separated by silica gel column chromatography (eluent:...

Embodiment 3

[0030] Example 3: Preparation of N-(1-acetyl-2,3,3-ylindoline-7-yl)-4-methylbenzenesulfonamide N-(1-acetyl-2,3,3-trimethylindolin -7-yl)-4-methylbenzenesulfonamide

[0031]

[0032] In the dried Schlenk tube, add the raw materials indoline (0.15 mmol, 30.4 mg), p-toluenesulfonamide (0.3 mmol, 51.1 mg), iodobenzene acetate (0.15 mmol, 48.3 mg), pentamethyl Cyclopentadienyl rhodium dichloride (5 mmol%, 4.6 mg), silver trifluoromethanesulfonate (20 mmol%, 7.7 mg), silver acetate (20 mmol%, 5.1 mg), acetic acid (0.45 mmol, 27 mg) 1.5 mL of 1,2-dichloroethane, and put the above-mentioned Schlenk tube at 100 o In a C oil bath, stir for about 16 h. The reaction was terminated, and the reaction solution was easily quenched with 2 mL of saturated ammonium chloride, and extracted several times with ethyl acetate (4 mL × 5), the organic phases were combined, and the solvent was removed on a rotary evaporator. Finally, after separation by silica gel column chromatography (eluent: et...

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Abstract

The invention discloses a method for preparing N-arylsulfonamide from indoline and arylsulfonamide, belonging to the technical field of C-H bond activation and functionalization catalyzed by a transition metal. The method includes adding 1-acetyl indoline, arylsulfonamide, bis[(pentamethylcyclopentadienyl)dichloro-rhodium], iodosobenzene diacetate, a silver salt and a solvent according to a ratiointo a Schlenk tube; putting the Schlenk tube in an oil bath and heating and stirring the materials in a nitrogen atmosphere for 16 h; terminating the reaction of the reaction solution with saturatedsaline to obtain a N-arylsulfonamide compound. N-arylsulfonamide compounds are prepared from the 1-acetyl indoline and the arylsulfonamide through direct C-H bond activation / amination for the first time. The method has advantages of simple and easily available raw materials and catalysts, mild reaction conditions, wide universality of reaction substrates, short reaction time, high yields of targetproducts, simple reaction operation, and simple aftertreatment.

Description

technical field [0001] The invention relates to the technical field of transition metal catalyzed C-H bond activation functionalization, in particular to the activation of C-H bonds and the construction of C-N bonds. Background technique [0002] N-arylsulfonamide compounds and their derivatives are an important class of compounds, which have various biological activities such as anticancer, antibacterial, anticonvulsant, and inhibition of HIV protease. (See: (a) Scozzafava, A.; Owa, T.; Mastrolorenzo, A.; Supuran, C. T. Curr. Med. Chem. 2003, 10, 925−953. (b) Supuran, C. T.; Casini, A.; Scozzafava, A. Med. Res. Rev. 2003, 5, 535−558.(c) Reddy, N. S. M.; Mallireddigari, R.; Cosenza, K. G.; Bell, S. C.; Reddy, E. P.; Reddy, M. V. R Bioorg. Med. Chem. Lett. 2004, 14, 4093−4097. (d) Stranix, B. R.; Lavallée, J.-F.; Sévigny, G.; Yelle, J.; Perron, V.; .; Wu, J. J. Bioorg. Med. Chem. Lett. 2006, 16, 3459−3462. (e) Siddiqui, N.; Pandeya, S. N.; Khan, S. A.; Stables, J.; Rana, A....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/08C07D209/88
CPCC07D209/08C07D209/88
Inventor 孙松董亚群成江于金涛
Owner CHANGZHOU UNIV
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