Preparation method for 4-substituted-7-azaindole

A technology of azaindole and organic solvent, applied in the field of synthesis of 4-substituted-7-azaindole, which can solve the problems of difficult industrialization, high price, and difficult removal, and achieve low cost, cheap price, and easy removal Effect

Inactive Publication Date: 2012-10-24
SHANGHAI DAMAS REAGENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] First use the oxidant 2-methyl-4-chlorophenoxyacetic acid (MCPA) to synthesize N-oxide-7-azaindole. This oxidant is relatively expensive, and because of its strong ultraviolet absorption, it is mixed in the product and is not easy to remove
In the second step, phosphorus oxychloride is used to react with N-oxidized-7-azaindole (without adding other solvents), and the yield is low, below 80%.
The cost of the whole route is relatively high, and it is not easy to industrialize

Method used

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  • Preparation method for 4-substituted-7-azaindole
  • Preparation method for 4-substituted-7-azaindole
  • Preparation method for 4-substituted-7-azaindole

Examples

Experimental program
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Embodiment 1

[0033] The synthesis of embodiment 1N-oxidation-7-azaindole

[0034]

[0035] 7-Azaindole (12.6 g, 0.102 mol) was added to tetrahydrofuran (120 ml), while the reaction was cooled to 5 ° C with an ice bath, hydrogen peroxide (6.1 g, 0.122 mol) was added dropwise to the reaction with stirring In the system, the temperature was slowly raised to room temperature, and reacted for 3 hours. The reaction solvent was spun to 30 ml on a rotary evaporator, and 60 ml of n-hexane was added thereto, and an off-white solid was precipitated. Filter and wash the filter cake with n-hexane, and dry the filter cake to obtain 12.8 g (0.0954 mol) of the target product, with a yield of 93.6%.

[0036] The synthesis of embodiment 24-chloro-7-azaindole

[0037]

[0038] N-oxide-7-azaindole (5.8 g, 0.043 mol) was added to acetonitrile (60 ml), and POCl was added under room temperature and stirring 3 (32.7 g, 0.215 mol). The reactant was heated to 80°C-100°C and reacted for 30 minutes, then di...

Embodiment 44

[0042] The synthesis of embodiment 44-methoxy group 7-azaindole

[0043]

[0044] 4-Bromo-7-azaindole (3.8 g, 0.019 mol) and sodium methoxide (1.3 g, 0.024 mol) were added to DMF (50 ml) at room temperature. The reaction temperature was raised to 110°C-130°C and reacted for 8 hours, then cooled to room temperature. DMF was removed by distillation under reduced pressure, and 30 ml of water was added to the residue. Extracted 3 times with 20ml of ethyl acetate, combined the organic phases, dried, and spin-dried to give a light yellow solid, which was recrystallized from methanol or ethanol to give 4-methoxy 7-azaindole (CAS 122379-63-9) 1.6 g, NMR spectrum as image 3 Shown, yield is 57.2%. The overall yield was 42.4%.

Embodiment 4

[0046] Other compounds were synthesized using the products of Examples 2-4 as raw materials.

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Abstract

The invention relates to the field of organic synthesis and medicine, and discloses a preparation method for 4-substituted-7-azaindole. Firstly, N-oxide-7-azaindole is prepared by employing 7-azaindole as a raw material and hydrogen peroxide as an oxidizing agent; then 4-halogenated-7-azaindole is synthesized by adding acetonitrile and phosphorus oxyhalides (POX3) and by using diisopropyl ethyl amine as a catalyst; and 4-methoxy-7-azaindole is synthesized by reacting the synthesized 4-halogenated-7-azaindole and alkoxide. The 4-substituted-7-azaindole synthesized by the method has high yield and low cost, and the method is easy for industrialization.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicine, in particular to a synthesis method of 4-substituted-7-azaindole. Background technique [0002] As an important member of the azaindole family, 7-azaindole is the isoelectronic body of indole and purine. Therefore, many molecules with biological activity can be formed by using 7-azaindole as the mother nucleus. [0003] Although the natural occurrences of 7-azaindole and its derivatives in nature are not as common as indole, they have attracted great interest because of their special physical and chemical properties and pharmaceutical activities. Especially 4-substituted 7-azaindole, such as 4-bromo-7-azaindole, 4-chloro-7-azaindole and 4-methoxy-7-azaindole, etc., It can be used as an intermediate in the synthesis of drugs with anticancer activity or in the treatment of immune system diseases. [0004] At present, there are two main methods for the synthesis of 4-substituted 7-az...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
Inventor 谢应波姚为建张庆张华
Owner SHANGHAI DAMAS REAGENT
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