5,12-dihydro-5-phenyl indole (3,2-a)carbazole synthesizing method

A technology of phenylindole and phenylcarbazole, applied in the field of organic chemical synthesis, can solve the problems of difficult removal of isomers, unsuitable operation, high cost, and achieve the effects of easy separation, avoidance of waste and fewer by-products

Active Publication Date: 2018-04-03
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

WO2013032284 reports a method for the synthesis of 5,12-dihydro-5-phenylindolo[3,2-a]carbazole using 3-boronic acid-N-phenylcarbazole as a starting material. The rate is low, t

Method used

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  • 5,12-dihydro-5-phenyl indole (3,2-a)carbazole synthesizing method
  • 5,12-dihydro-5-phenyl indole (3,2-a)carbazole synthesizing method

Examples

Experimental program
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Example Embodiment

[0021] Example 1

[0022] Dissolve 51.7 g (0.2 mol) 4-amino-N-phenylcarbazole in 200 mL acetonitrile in a 1 L three-necked flask, add 36.4 g (0.18 mol) 40% hydrobromic acid aqueous solution by mass, and control the reaction temperature- Slowly add 18.4 mL (0.18 mol) of 30% hydrogen peroxide at 20°C. After the addition is complete, the temperature will rise naturally and the reaction will be overnight. The reaction solution is washed with aqueous sodium bisulfite solution, the organic layer is separated, and hydrochloric acid is added to obtain 3-bromo-4-amino -N-phenylcarbazole hydrochloride, 61.9 g after drying; under argon protection, 61.9 g (0.16 mol) 3-bromo-4-amino-N-phenylcarbazole hydrochloride, 33.1 g o- Bromophenylboronic acid, 20.2 g of cesium carbonate, 200 mL of N-methylpyrrolidone solvent were added to a 1 L three-necked flask, replacing the air system, and then adding 0.04 g of palladium acetate and 0.16 g (R,R)-1,2 at 20 ℃ -Bis[(2-methoxyphenyl)phenylphosphino]eth...

Example Embodiment

[0024] Example 2

[0025] Dissolve 129.2 g (0.5 mol) 4-amino-N-phenylcarbazole in 1000 mL acetonitrile in a 2 L three-necked flask, add 95.1 g (0.47 mol) 40% hydrobromic acid aqueous solution with mass percentage, and control the reaction temperature. Slowly add 48.0 mL (0.47 mol) of 30% hydrogen peroxide at ℃. After the addition is complete, the temperature is naturally heated 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 3-bromo-4-amino- N-phenylcarbazole hydrochloride, 160.6 g after drying; under argon protection, 160.6 g (0.42 mol) 3-bromo-4-amino-N-phenylcarbazole hydrochloride, 84.3 g o-bromide Phenylboronic acid, 55.2g cesium carbonate, 800 mL N-methylpyrrolidone solvent were added to a 2 L three-necked flask, the air system was replaced, and then 0.5 g palladium acetate and 1.9 g (R,R)-1,2-bis [(2-Methoxyphenyl)phenylphosphino]ethane, reflux reaction, li...

Example Embodiment

[0026] Example 3

[0027] Dissolve 206.7 g (0.8 mol) 4-amino-N-phenylcarbazole in 1600 mL acetonitrile in a 5 L three-necked flask, add 137.5 g (0.68 mol) 40% hydrobromic acid aqueous solution with mass percentage, and control the reaction temperature- Slowly add 89.8mL (0.88mol) 30% hydrogen peroxide dropwise at 20°C. After the dropwise addition is complete, the temperature will rise naturally and the reaction will be overnight. The reaction solution is washed with aqueous sodium bisulfite solution, the organic layer is separated, and hydrochloric acid is added to obtain 3-bromo-4-amino -N-phenylcarbazole hydrochloride, 248.1 g after drying; under argon protection, 248.1 g (0.66 mol) 3-bromo-4-amino-N-phenylcarbazole hydrochloride, 132.3 g o- Bromophenylboronic acid, 71.5 g of cesium carbonate, 1500 mL of N-methylpyrrolidone solvent were added to a 5 L three-necked flask, the air system was replaced, and 1.5 g of palladium acetate and 6.0 g (R,R)-1,2- Bis[(2-methoxyphenyl)pheny...

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Abstract

The invention discloses a 5,12-dihydro-5-phenyl indole (3,2-a)carbazole production method and belongs to the field of organic chemical synthesis. The 5,12-dihydro-5-phenyl indole (3,2-a)carbazole is synthesized by the following steps of utilizing 4-amino-N-phenyl carbazole as a beginning raw material, brominating and Suzuki and Buchwald coupling. The synthesizing method ahs the advantages of little side reaction in a reaction process, simpleness in operation and high yield. The synthesizing 5,12-dihydro-5-phenyl indole (3,2-a)carbazole can be applied to the fields of organic photoelectric materials, medicine and the like and is an important intermediate of carbazole photoelectric materials, medicine and pesticides.

Description

technical field [0001] The present invention relates to a preparation method of a class of indolo[3,2-a]carbazole derivatives, in particular to a 5,12-dihydro-5-phenylindolo[3,2-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 derivativ...

Claims

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Application Information

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IPC IPC(8): C07D487/04
Inventor 杨振强孙敏青屈凤波马欣李奎杨瑞娜樊燕鸽席振峰
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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