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Synthetic method for 5H-benzo[b]carbazole

A kind of synthesis method, the technology of carbazole, is applied in the synthesis field of 5H-benzo [b] carbazole

Inactive Publication Date: 2019-06-11
SUZHOU SY PHARMA TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In order to solve the problem of the synthetic method of existing 5H-benzo[b]carbazole, the present invention provides a kind of synthetic method of 5H-benzo[b]carbazole

Method used

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  • Synthetic method for 5H-benzo[b]carbazole
  • Synthetic method for 5H-benzo[b]carbazole
  • Synthetic method for 5H-benzo[b]carbazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A kind of synthetic method of 5H-benzo [b] carbazole, comprises the steps:

[0026] ⅰ. Add 1.72g of 2-naphthylboronic acid, 1.72g of o-bromoaniline, 2.77g of potassium carbonate and 60mg of tetraphenylphosphine palladium in a 250ml round bottom flask, and add 80mL of N,N-dimethylformaldehyde at room temperature Stir the amide to fully dissolve 2-naphthylboronic acid, o-bromoaniline, potassium carbonate and tetrakistriphenylphosphine palladium, then add 50mL of pure water to wash, extract with ethyl acetate, dry and concentrate, ethyl acetate has excellent solubility, Quick-drying type, used as an extractor to extract the product, after concentrated column chromatography, in the process of eluting the sample from the column, according to the different distribution coefficients of the components in the solution in the stationary phase and the mobile phase, they are repeatedly distributed , the different components were repeatedly distributed to obtain off-white solid prod...

Embodiment 2

[0032] ⅰ. Add 17.2g of 2-naphthylboronic acid, 17.2g of o-bromoaniline, 27.7g of potassium carbonate and 1.2g of tetrakistriphenylphosphine palladium in a 250ml round bottom flask, and add 2L of N,N-dimethyl Stir the formamide to fully dissolve 2-naphthylboronic acid, o-bromoaniline, potassium carbonate and tetrakistriphenylphosphine palladium, then add 50mL of pure water to wash, extract with ethyl acetate, dry and concentrate, and obtain off-white solid through concentration column chromatography product a

[0033] ⅱ. Get the product a that 16.5g step i obtains Dissolve in 2L of dichloromethane, add 6.5g of acetyl chloride dropwise at room temperature, quench with saturated aqueous sodium carbonate solution after fully reacting, wash with 500mL of distilled water three times, and dry the organic phase obtained by anhydrous sodium sulfate, then concentrate the column layer Analysis obtains the white solid product b after acetyl protection

[0034] ⅲ. In the reaction ve...

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Abstract

The invention provides a synthetic method for 5H-benzo[b]carbazole, and relates to the technical field of chemical synthesis. The method comprises the following steps: adding 2-naphthaleneboronic acid, o-bromoaniline, potassium carbonate and tetrakistriphenylphosphine palladium into a flask, adding N,N-dimethylformamide, performing stirring, performing washing by using purified water, performing extraction by using ethyl acetate, performing dry concentration, performing concentration column chromatography, dissolving the product a into dichloromethane, adding acetyl chloride dropwise, performing a full reaction, performing quenching by using a saturated sodium carbonate aqueous solution, drying the organic phase by using anhydrous sodium sulfate, performing concentration column chromatography to obtain an acetyl-protected white solid product b, adding palladium acetate and toluene, performing heating reflux under stirring, performing filtration concentration, performing column chromatography to obtain a product c, adding methanol into the ring-off product c and equivalent sodium hydroxide for dissolution, and performing separation to obtain the product d, that is, the 5H-benzo[b]carbazole. The method provided by the invention has low costs, high selectivity and simple operation.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and the invention relates to a synthesis method of 5H-benzo[b]carbazole. Background technique [0002] Both carbazole and its derivatives have unique structures that make them important precursors in synthetic chemistry and also serve as widely used ligands in metal-catalyzed reactions. Therefore, synthetic chemistry based on carbazole is an important hotspot in modern organic synthesis. These derivatives can be widely used in medicine, pesticides, physical chemistry, material chemistry and life sciences, and have very good development and application prospects. [0003] 5H-Benzo[b]carbazole is an important derivative of carbazole, which can be used in many aspects such as material science, metal-organic ligands, life science, etc. Its structural formula d is as follows: [0004] [0005] Its synthesis method is mainly reported by Prasad Appukkuttan et al. (Synlett, (1), 127-133; 2...

Claims

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Application Information

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IPC IPC(8): C07D209/80
Inventor 姚梁锋张家豪施敏
Owner SUZHOU SY PHARMA TECH CO LTD
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