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Preparation method for 7-azaindole

A technology for azaindole and compounds, which is applied in the field of compound preparation, can solve the problems of high reaction temperature, high energy consumption, and low product purity, and achieve the effects of mild and controllable reaction conditions, shortened synthetic routes, and simple post-treatment

Inactive Publication Date: 2018-12-11
EAST CHINA NORMAL UNIV +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The reaction product of 2-amino-3-picoline and triethyl orthoformate in step a of this route is unstable and easily deteriorated, resulting in low purity of the product in reaction b; in step c, the reaction condition is to reflux at 250°C Close the ring, the reaction temperature is too high, difficult to control, high energy consumption
These shortcomings all bring inconvenience to its industrialized production

Method used

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  • Preparation method for 7-azaindole
  • Preparation method for 7-azaindole
  • Preparation method for 7-azaindole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1.1 In a single-necked bottle, add 2.0g 2-amino-3-picoline and 2.5g N-methylformanilide into 40mL dichloromethane, stir and add 3.15g P 2 o 5 . After reacting for 4 hours, the reaction system was slowly poured into 40 mL of ammonia water, and the insoluble matter was removed by suction filtration. The organic layer was separated, washed twice with water, dried over anhydrous sodium sulfate, and evaporated to dryness to obtain 2.91 g of a light yellow solid with a yield of 70%.

[0024] 1 H NMR (500MHz, CDCl 3 )δ8.91(s,1H),8.16(d,J=3.9Hz,1H),7.46(d,J=7.2Hz,1H),7.39(t,J=7.9Hz,2H),7.27(d, J=7.9Hz, 2H), 7.17(t, J=7.4Hz, 1H), 6.89-6.91(m, 1H), 3.59(s, 3H), 2.39(s, 3H).

[0025] 1.2 In a single-necked bottle, add 2.0g 2-amino-3-picoline and 2.5g N-methylformanilide into 40mL dichloromethane, stir and add 4.62g PCl under ice-water bath 5 . After reacting for 4 hours, the reaction system was slowly poured into 40 mL of ammonia water, and the insoluble matter was removed ...

Embodiment 2

[0032] 2.1 In a three-necked flask, under the protection of nitrogen, dissolve 5g of N-methyl-N-phenyl-N'-(2-(3-methylpyridinyl)yl)formamidine in 30mL of dry tetrahydrofuran, drop into -20 ℃. Then, 13 mL of n-butyllithium (2.5 M) was slowly added dropwise, and after 5 hours of reaction, the reaction system was poured into 1 M citric acid aqueous solution to quench the reaction. Extracted with ethyl acetate, separated the organic layer, back-extracted the aqueous layer once, combined the organic layers, dried over anhydrous sodium sulfate, and evaporated to dryness to obtain 1.04 g of 7-azaindole with a yield of 40%.

[0033] 1 H NMR (400MHz, CDCl 3 )δ12.13(s,1H),8.29(dd,J=4.7,1.2Hz,1H),7.94(dd,J=7.8,1.4Hz,1H),7.34(d,J=3.5Hz,1H), 7.07 (dd, J=4.8Hz, 1H), 6.49 (d, J=3.5Hz, 1H).

[0034] 2.2 In a three-necked flask, under the protection of nitrogen, dissolve 5g of N-methyl-N-phenyl-N'-(2-(3-methylpyridinyl)yl)formamidine in 30mL of dry tetrahydrofuran, and drop into -20 ℃. T...

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Abstract

The invention discloses a preparation method for 7-azaindole, and belongs to technical field of the medicinal chemistry synthesis. The preparation method comprises the following steps: using a compound I, namely 2-amino-3-methylpyridine and N-methylformanilide, to perform an addition elimination reaction under the action of a dehydrating agent, to obtain a compound II; performing intramolecular ring closure on the compound II under the action of strong base, to obtain a target compound III. The preparation method is capable of acquiring the target product through two-step synthesis only. The method is simple in post-treatment, less in side reaction, high in yield, and in comply with requirements of industrial production. (The formula is shown in the description.).

Description

technical field [0001] The invention relates to the technical field of compound preparation, in particular to a preparation method of 7-azaindole. Background technique [0002] 7-Azaindole series compounds are an important class of heterocyclic intermediates with good biological and medicinal value, and are the core structure of many drugs, such as antineoplastic drugs, dopamine D4 receptors, p38 kinase inhibitors, blood coagulation Enzyme inhibitors, etc., so it has a wide range of application value in medical research. [0003] At present, there are relatively few methods for synthesizing 7-azaindole at home and abroad, and a Joc document (R.R.Lorenz, B.F.Tullar, C.F.Koelsch, S.Archer, J. Org. Chem. 1965,30,2531) reported the following method: [0004] [0005] The reaction product of 2-amino-3-picoline and triethyl orthoformate in step a of this route is unstable and easily deteriorated, resulting in low purity of the product in reaction b; in step c, the reaction co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 罗宇朱皓庭周朴李晓林秦凌雁占莉吴文萱李倩康立涛杨世琼
Owner EAST CHINA NORMAL UNIV
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