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Preparation method of 3-iodo-5-bromo-4, 7-diazaindole

A technology of diazepine and indole, applied in the field of pharmaceutical preparations, can solve the problems of low synthesis yield and the like, and achieve the effects of high reaction yield, easy product and short reaction process route

Inactive Publication Date: 2012-08-08
STONE LAKE PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Participate in figure 2 , in 2011, the synthesis method of this compound was also reported in the international patent WO2011 / 149950A2, and the above method was appropriately improved, but the synthesis yield was still low (minimum to 31%)

Method used

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  • Preparation method of 3-iodo-5-bromo-4, 7-diazaindole
  • Preparation method of 3-iodo-5-bromo-4, 7-diazaindole
  • Preparation method of 3-iodo-5-bromo-4, 7-diazaindole

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Embodiment Construction

[0025] See attached image 3 , the preparation method of the 3-iodo-5-bromo-4,7-diazaindole of the invention comprises the following steps:

[0026] Step (1) In a flask, add 38.0 g of the raw material 2-aminopyrazine and dissolve with 500 mL of dimethyl sulfoxide (DMSO) and 20 mL of H 2 After O was dissolved, 149.5 g of N-bromosuccinimide (NBS) was added in batches, and the reaction temperature was controlled below 15 °C. After the addition was complete, it was stirred at room temperature, followed by TLC spotting. After the reaction was completed, it was quenched with ice water (300 mL), and the layers were separated after standing. The aqueous phase was extracted with ethyl acetate (200 mL×3), and the organic phases were combined and washed with 5% Na 2 CO 3 solution and H 2 After washing with O, anhydrous Na 2 SO 4 dry. After filtration, the solvent was removed in vacuo to obtain a crude product, which was recrystallized with a small amount of absolute ethanol (EtOH) ...

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Abstract

The invention discloses a preparation method of 3-iodo-5-bromo-4, 7-diazaindole. The preparation method comprises the following steps that 1), 2-aminopyrazine and N-bromosuccinimide undergo a bromination reaction to produce 2-amino-3, 5-dibromopyrazine; 2) 2-amino-3, 5-dibromopyrazine undergoes a synthesis reaction in the presence of acetaldehyde, potassium tert-butoxide and an N-heterocyclic carbine-Pd (NHC-Pd) compound as a catalyst to produce 5-bromo-4, 7-diazaindole; and 5-bromo-4, 7-diazaindole undergoes an iodination reaction to produce 3-iodo-5-bromo-4, 7-diazaindole. The preparation method has the advantages that raw material prices are low; a reaction process route is short; a reaction yield is high; and products can be separated easily.

Description

technical field [0001] The invention relates to pharmaceutical preparations, in particular to a preparation method of 3-iodo-5-bromo-4,7-diazaindole. Background technique [0002] Studies have confirmed that azaindole compounds have anti-cancer, anti-bacterial, anti-viral, and treatment of hypertension and other uses in terms of pharmacological effects. Due to the various physiological activities of azaindole alkaloids, people not only use their plants to treat diseases, but also directly use these extracted alkaloids to treat diseases, and carry out structural modification on them to develop more drugs. In the process of drug development, azaindole is one of the important structures, and many drugs are based on it. [0003] The research on the preparation method of azaindole mainly contains the following aspects in the published bibliographical reports at present: [0004] See attached figure 1 , as early as 2006, the international patent WO2006 / 015124A2 reported the pre...

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Application Information

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IPC IPC(8): C07D487/04
Inventor 吕少波邱玲玲
Owner STONE LAKE PHARMA TECH
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