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Synthesis method of 11,12-dihydro-11-phenylindole [2,3-a]carbazole

A technology of phenylindole and phenylcarbazole, applied in the field of organic chemical synthesis, can solve the problems of unsuitable operation, cumbersome process and high cost, and achieve the effects of avoiding waste, simple operation process and less by-products

Active Publication Date: 2018-06-12
PUYANG HUICHENG ELECTRONICS MATERIAL
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

KR2017001101 reported a method for the synthesis of 11,12-dihydro-11-phenylindolo[2,3-a]carbazole using 2-bromo-N-phenylcarbazole as a starting material. The rate is low, the process is cumbersome in actual use, it is not suitable for operation, and the cost is high, so it is necessary to explore new methods suitable for industrial production

Method used

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  • Synthesis method of 11,12-dihydro-11-phenylindole [2,3-a]carbazole
  • Synthesis method of 11,12-dihydro-11-phenylindole [2,3-a]carbazole

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Experimental program
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Effect test

Embodiment 1

[0022] Dissolve 77.5 g (0.3 mol) of 1-amino-N-phenylcarbazole in 300 mL of acetonitrile in a 2 L three-necked flask, add 52.6 g (0.26 mol) of 40% hydrobromic acid aqueous solution by mass, and control the reaction temperature- Slowly add 27.6 mL (0.27 mol) of 30% hydrogen peroxide dropwise at 20 °C. After the dropwise addition is complete, the temperature is naturally raised to react overnight. The reaction solution is washed with aqueous sodium bisulfite solution, the organic layer is separated, and hydrochloric acid is added to obtain 1-amino-2-bromo -N-phenylcarbazole hydrochloride, 97.1 g after drying; under argon protection, 97.1 g (0.25 mol) 1-amino-2-bromo-N-phenylcarbazole hydrochloride, 50.2 g ( 0.25 mol) o-bromophenylboronic acid, 36.9 g cesium carbonate, and 250 mL N-methylpyrrolidone solvent were added to a 2 L three-neck flask to replace the air system, and then 0.05 g palladium acetate and 0.23 g (R,R)- 1,2-bis[(2-methoxyphenyl)phenylphosphino]ethane, reflux reac...

Embodiment 2

[0026] In a 5 L three-necked flask, 155.0 g (0.6 mol) of 1-amino-N-phenylcarbazole was dissolved in 1200 mL of acetonitrile, and 111.2 g (0.55 mol) of 40% hydrobromic acid aqueous solution was added to control the reaction temperature- Slowly add 61.3mL (0.6 mol) of 30% hydrogen peroxide dropwise at 20°C. After the dropwise addition is complete, the temperature is naturally raised to react overnight. The reaction solution is washed with aqueous sodium bisulfite solution, the organic layer is separated, and hydrochloric acid is added to obtain 1-amino-2-bromo -N-phenylcarbazole hydrochloride, 186.8 g after drying; under argon protection, 186.8 g (0.5 mol) 1-amino-2-bromo-N-phenylcarbazole hydrochloride, 100.4 g ( Add 0.5 mol) o-bromophenylboronic acid, 65.0 g (0.2 mol) cesium carbonate, and 1000 mL N-methylpyrrolidone solvent into a 5 L three-necked flask, replace the air system, and then add 0.1 g palladium acetate and 2.3 g (R ,R)-1,2-bis[(2-methoxyphenyl)phenylphosphino]etha...

Embodiment 3

[0028]In a 5 L three-necked flask, 258.3 g (1.0 mol) of 1-amino-N-phenylcarbazole was dissolved in 2000 mL of acetonitrile, 192.1 g (0.95 mol) of 40% hydrobromic acid aqueous solution was added, and the reaction temperature was controlled at 0 Slowly add 112.3 mL (1.1 mol) of 30% hydrogen peroxide dropwise at ℃. After the dropwise addition is complete, the reaction temperature is naturally raised overnight. N-phenylcarbazole hydrochloride, 313.9 g after drying; under the protection of argon, 313.9 g (0.84mol) 1-amino-2-bromo-N-phenylcarbazole hydrochloride, 168.7 g o-bromo Add phenylboronic acid, 91.0 g of cesium carbonate, and 2000 mL of N-methylpyrrolidone solvent into a 5 L three-neck flask to replace the air system, then add 1.9 g of palladium acetate and 7.7 g of (R,R)-1,2-bis [(2-Methoxyphenyl) phenylphosphino]ethane, reflux reaction, detection by liquid chromatography, after the end, add 2000 mL ice water to terminate the reaction, extract with 2000 mL methylene chlorid...

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Abstract

The invention discloses a production method of 11,12-dihydro-11-phenylindole [2,3-a]carbazole. The method belongs to the field of organic chemical synthesis, and comprises the steps of adopting 1-amino-N-phenylcarbazole as a starting material, and carrying out bromination reaction, Suzuki coupling reaction and Buchwald coupling reaction to synthesize the 11,12-dihydro-11-phenylindole [2,3-a]carbazole. During the reaction process, the method is less in side reaction, simple to operate and high in yield. The synthesized 11,12-dihydro-11-phenylindole [2,3-a]carbazole can be applied to the fieldssuch as organic optoelectronic materials and medicines, and is an important intermediate for carbazole photoelectric materials, medicines and pesticides.

Description

technical field [0001] The present invention relates to a preparation method of a class of indolo[2,3-a]carbazole derivatives, in particular to a 11,12-dihydro-11-phenylindolo[2,3-a]carbazole The synthetic method belongs to the field of organic chemical synthesis. Background technique [0002] Carbazole is an important heterocyclic compound, which widely exists in natural products and medicinal chemical molecules, and has obvious biological and pharmacological activities. In addition, carbazole and its derivatives have excellent light spot properties, which have a large π-electron conjugated system and strong intramolecular electron transfer characteristics. From the structural point of view, the electrophilic N atom of carbazole is induced by the Absorb the electrons on the double bond; on the other hand, due to the p-π conjugation effect, the unshared electrons of the N atom donate to the double bond, making the double bond rich in electrons. Therefore, carbazole derivat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
Inventor 杨振强陈辉屈凤波周铎陈鹏丽王朝杰杨瑞娜王从洋
Owner PUYANG HUICHENG ELECTRONICS MATERIAL
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