Non-correspondence selective synthesis of 1-aryl-1H-pyridine[3,4-b]indole derivative

An aryl and pyridine technology, applied in the field of asymmetric synthesis, can solve problems such as difference in activity, and achieve good economic and social benefits.

Active Publication Date: 2017-12-01
嘉兴慧泉生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As described in the aforementioned invention patent CN201610804063.1, Example 9, MIPO-6-1 and MIPO-6-2 are a pair of diastereoisomers with 6-fold difference in activity

Method used

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  • Non-correspondence selective synthesis of 1-aryl-1H-pyridine[3,4-b]indole derivative
  • Non-correspondence selective synthesis of 1-aryl-1H-pyridine[3,4-b]indole derivative
  • Non-correspondence selective synthesis of 1-aryl-1H-pyridine[3,4-b]indole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Synthesis of compound 2-isopropyl-4-tert-butylphenol (reaction formula 10)

[0035]

[0036] Add 2-isopropylphenol (68.1 g, 0.5 mol) and tert-butyl chloride (55.6 g, 0.6 mol) successively in a three-necked flask equipped with high-purity nitrogen protection and mechanical stirring, and add chlorine in batches at room temperature Aluminum chloride (6.0g) was added, stirred at room temperature for 30 minutes; heated at 55°C, and reacted for 45 minutes. After the reaction solution was cooled to room temperature, the reaction solution was poured into 300 g of ice-water mixture, stirred thoroughly, extracted with 3*200 mL ether, and the combined ether layer was successively washed with 400 mL of saturated sodium chloride aqueous solution and 400 mL of saturated carbonic acid Wash with sodium hydrogen aqueous solution, dry the ether layer with magnesium sulfate, filter, and remove the solvent by rotary evaporation to obtain a crude product. The crude product is ...

Embodiment 2

[0037] Example 2: Synthesis of compound 2-hydroxy-3-isopropyl-5-tert-butylbenzaldehyde (reaction formula 11)

[0038]

[0039] Add anhydrous THF (150 mL), anhydrous magnesium chloride (9.51 g, 100 mmol), paraformaldehyde (4.50 g, 150 mmol) sequentially into a four-neck flask equipped with high-purity nitrogen protection and mechanical stirring, Triethylamine (11.20g, 100 mmol) was added dropwise into the dropping funnel, the mixture was stirred at 25°C for 20 minutes, and 2-isopropyl-4-tert-butylphenol (9.62g, 50 mmol) was added dropwise in THF (50 mL) solution, heated to reflux, and reacted for 2.5 hours. After the reaction solution was cooled to room temperature, the reaction solution was poured into 300 mL of 1 M dilute hydrochloric acid, stirred thoroughly, extracted with 3*150 mL ether, and the combined ether layer was successively washed with 2*200 mL saturated sodium chloride aqueous solution, Wash with 200 mL saturated aqueous sodium bicarbonate solution, dry the o...

Embodiment 3

[0040] Example 3: Synthesis of chiral ligand compound L (reaction formula 12)

[0041]

[0042] Add 2-hydroxy-3-isopropyl-5-tert-butylbenzaldehyde (3.88 g, 17.6 mmol) and a magnetic stirrer into a round bottom flask, then add 25 mL of absolute ethanol to dissolve it, and then add (l R ,2 R )-1,2-cyclohexanediamine (0.91 g, 8 mmol). The reaction was stirred at 40 °C, and the reaction was monitored by thin layer chromatography (TLC) until the starting material (l R ,2 R )-1,2-cyclohexanediamine reacted completely. Appropriate concentration, cooling and crystallization, suction filtration to obtain an orange solid, 2.95 g, yield 71%.

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Abstract

The invention discloses an asymmetric synthesis method for synthesizing 1-aryl-1H-pyridine[3,4-b]indole-3-carboxylic acid methyl ester derivatives containing two chiral centers by taking (R)-tryptophan methyl ester and aldehyde as main starting raw materials, taking chiral Lewis acid Salen-Mn as a catalyst and taking (R)-alpha-methyl-4-nitrophenylacetic acid as a chiral additive. Compared with the prior art, the reaction yield is improved and the non-correspondence selectivity of the reaction is remarkably improved.

Description

technical field [0001] The present invention relates to the synthesis of 1H-pyridine[3,4-b]indole compounds, especially a class of 1-aryl-1H-pyridine[3,4-b]indole derivatives containing two chiral centers Compound synthesis belongs to the field of asymmetric synthesis. Background technique [0002] Chirality is a basic feature of nature. If a molecule cannot coincide with its mirror image, the molecule is called a chiral molecule. Many bioactive molecules in nature are chiral molecules. When the atomic composition of two molecules is the same, but the spatial structure is different, and the relationship between them is a real object and a mirror image, which can also be compared to the relationship between left and right hands, these two molecules are enantiomers of each other. Almost all biomolecules that play a key role in the generation and evolution of life are chiral, such as naturally occurring sugars ( D )-configuration, the amino acid is ( L )-configuration, whil...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04B01J31/22
CPCB01J31/2217B01J37/30B01J2231/34B01J2531/0252B01J2531/72C07B2200/07C07D471/04
Inventor 杨维清杨梓轩佘明虎刘荣霞张啸晨王宏任川洪
Owner 嘉兴慧泉生物科技有限公司
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