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Practical synthesis method of 3-acetyl-4-azaindole

A technique for the synthesis of azaindole, which is applied in the fields of medicine and chemical industry, can solve the problems of unavailable products, unsuitable for scale-up and industrial production, and low reaction yield, and achieve mild conditions, shorten the production process, and improve the reaction rate. The effect of temperature

Inactive Publication Date: 2015-02-25
苏州科捷生物医药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] We have tried this method many times and found that the reaction yield is extremely low, and almost no product can be obtained. At the same time, silica gel column chromatography is required to separate the product, which is not suitable for scale-up and industrial production.

Method used

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  • Practical synthesis method of 3-acetyl-4-azaindole
  • Practical synthesis method of 3-acetyl-4-azaindole
  • Practical synthesis method of 3-acetyl-4-azaindole

Examples

Experimental program
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Effect test

Embodiment 1

[0015] Embodiment 1: synthetic 4-azaindole (compound 2)

[0016]

[0017] 2-Methyl-3-nitropyridine (23.4 g, 0.17 mol), DMF-DMA (60 g, 0.51 mol) and DMF (100 mL) were heated to 90° C. and stirred for 8 hours. Cool to room temperature, pour the reaction solution into 300 ml of cold water, filter with suction to obtain a red solid, dissolve the solid in ethanol (500 ml), add 10% Pd / C (5 g), and stir at room temperature for 10 hours under a hydrogen atmosphere , suction filtration (spread a layer of diatomaceous earth), wash with ethanol, and concentrate to obtain 18.1 g of brown solid 4-azaindole, yield: 90.5%.

[0018] EI-MS MS (m / z): 119.1 (M + )

[0019] 1 H-NMR (DMSO-d6, 400MHz): δ8.29~8.27(m, 1H), 7.76(d, 1H), 7.61(d, 1H), 7.08~7.04(m, 1H), 6.54~6.52(m , 1H).

Embodiment 2

[0020] Embodiment 2: Synthesis of 3-acetyl-4-azaindole (compound 3)

[0021]

[0022] Add 4-azaindole (21g, 0.18mol) to anhydrous aluminum chloride (106.8g, 0.80mol) and suspend in dichloroethane (800ml), heat to 50°C and stir for 1 hour, then cool to room temperature , dropwise added acetyl chloride (18.8g, 0.24 moles), heated to 50°C and stirred for 2 hours after the addition, cooled, slowly added dropwise methanol (300 ml) to quench the reaction, concentrated to dryness, added water (100 ml), Add sodium carbonate solution dropwise until a large amount of solids precipitate, filter with suction, wash the solid with ethyl acetate (400 ml), discard the solid, wash the ethyl acetate layer with saturated brine (50 ml), dry over anhydrous sodium sulfate, and filter with suction , concentrated to obtain a crude product, added n-hexane (60 ml), stirred, suction filtered, and dried to obtain 20.2 g of off-white solid 3-acetyl-4-azaindole, yield: 70.1%.

[0023] EI-MS MS (m / z): 1...

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Abstract

The invention discloses a practical synthesis method of 3-acetyl-4-azaindole. The synthesis method comprises the following steps: taking 2-methyl-3-nitropyridine as the primary raw material, making 2-methyl-3-nitropyridine carry out condensation reactions with DMF-DMA, then subjecting the reaction products to hydrogenation and ring-closure reactions in the presence of a catalyst Pd / C so as to obtain 4-azaindole, and finally subjecting 4-azaindole to Friedel-Crafts reactions so as to obtain 3-acetyl-4-azaindole. The provided method has the advantages of mild conditions, easily-available raw materials, low cost, high yield, and convenient operation, and thus is suitable for industrial production.

Description

technical field [0001] The invention relates to a practical synthesis method of 3-acetyl-4-azaindole, which belongs to the technical fields of medicine and chemical industry. Background technique [0002] 3-acetyl-4-azaindole is a very important intermediate, which is widely used in the field of biomedicine (JMC2012, 55: 9531-9540; BMCL2013, 23: 213-217; US2004 / 63744; US2010 / 22581; WO2011 / 73092), can be used to synthesize complement factor D inhibitors to treat age-related macular degeneration (WO2012093101); can also be used to synthesize FAAH enzyme inhibitors for the treatment of pain, inflammation, neurodegenerative diseases, etc. (WO2012 / 88469 ). [0003] The synthesis of 3-acetyl-4-azaindole, the method reported in literature (JOC2002,67:6226-6227) is: use 4-azaindole as raw material, methylene chloride as solvent, anhydrous trichloride Aluminum is used as a catalyst, reacts with acetyl chloride at room temperature for several hours, and is separated by silica gel co...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 邵东黄传满
Owner 苏州科捷生物医药有限公司
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