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Synthesizing method of (E)-5-methyl-1H-pyrrolo-[2,3-b] pyridine-3-formaldoxime

A technology of formaldehyde oxime and pyrrole, which is applied in the synthesis field of (E)-5-methyl-1H-pyrrolo[2,3-b]pyridine-3-formaldehyde oxime, and can solve problems such as no effective synthetic method. , to achieve the effect of cheap raw materials and simple purification

Inactive Publication Date: 2017-08-18
KANGHUA SHANGHAI DRUG RES DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide a synthetic method of (E)-5-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde oxime, which mainly solves the technical problem that no effective synthetic method has been seen.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] step 1:

[0012] Add 2-amino-5-methylpyridine (70.0 g, 654 mmol) and dichloromethane (150 mL) into a three-necked flask; add liquid bromine (36.0 mL, 698 mmol) in an ice bath. The reaction solution was stirred at room temperature for 30 minutes. Saturated sodium sulfite solution (100 mL) was added; the aqueous phase was extracted with dichloromethane (100 mL x 3), the organic phases were combined, washed with water (100 mL) and saturated brine (100 mL), dried over sodium sulfate, and filtered. After spin-drying, a yellow solid, Compound 1 (103.0 g, 550 mmol, 84 %) was obtained. The product was directly used in the next reaction. 1 H NMR (400 MHz, CDCl 3 ) 2.18 (s, 3H), 4.89 (br,2H), 7.51 (d, J = 1.2 Hz, 1H), 7.82 (d, J = 1.6 Hz, 1H) ppm;

[0013] Step 2:

[0014] Add compound 1 (55.4 g, 300 mmol), diisopropylamine (60 mL), trimethylethynyl silicon (60 mL, 420.0 mmol), bistriphenylphosphine palladium dichloride (2.04 g, 2.9 mmol) and cuprous iodide (0.55g, 2.9 mmol...

Embodiment 2

[0021] Embodiment 2: the first step reaction time is 10 minutes; the second step reaction temperature is 90°C; the third step reaction time is 15 minutes, the third step reaction temperature is 70°C; the fourth step reaction time is 3 hours; the fifth step For the reaction, compound 4 was first dissolved in methanol by heating at 60°C, then hydroxylamine hydrochloride and sodium acetate were added, and reacted at room temperature for 15 minutes. All the other are with embodiment 1.

Embodiment 3

[0022] Embodiment 3: the first step reaction time is 30 minutes; the second step reaction temperature is 70°C; the third step reaction time is 5 minutes, the third step reaction temperature is 90°C; the fourth step reaction time is 5 hours; the fifth step For the reaction, compound 4 was first dissolved in methanol by heating at 70°C, then hydroxylamine hydrochloride and sodium acetate were added, and reacted at room temperature for 5 minutes. All the other are with embodiment 1.

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Abstract

The invention relates to a synthesizing method of (E)-5-methyl-1H-pyrrolo-[2,3-b] pyridine-3-formaldoxime, which solves the technical problem that an effective synthesizing method is not discovered at present. The synthesizing method provided by the invention comprises the following steps: brominating 2-amino-5-picoline, so as to obtain a compound 1; performing a reaction on the compound 1 and trimethylsilylacetylene under a condition of a Sonogashira coupling reaction, so as to generate a compound 2; performing a reaction on the compound 2 and sodium hydride to form a pyrrole ring, so as to generate a compound 3; performing a reaction on the compound 3 and urotropine, so as to generate a compound 4; performing the compound 4, hydroxylamine hydrochloride and sodium acetate, so as to obtain the target product (E)-5-methyl-1H-pyrrolo-[2,3-b] pyridine-3-formaldoxime. As a sodium acetate, the (E)-5-methyl-1H-pyrrolo-[2,3-b] pyridine-3-formaldoxime is widely applied in the pharmaceutical industry.

Description

technical field [0001] The present invention relates to the synthesis of (E)-5-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde oxime. Background technique [0002] (E)-5-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde oxime (CAS: 1198098-52-0), as a pharmaceutical intermediate, is widely used in the pharmaceutical industry. But so far there is no public report about its synthesis method. Contents of the invention [0003] The purpose of the present invention is to provide a synthetic method of (E)-5-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde oxime, which mainly solves the technical problem that no effective synthetic method has been seen. . [0004] The technical solution of the present invention is: a synthetic method of (E)-5-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde oxime, which is characterized in that it comprises the following steps: the first step, 2 -Amino-5-methylpyridine reacts with bromine in dichloromethane, reacts at room temperature, removes exc...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 马敬祥
Owner KANGHUA SHANGHAI DRUG RES DEV CO LTD
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