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Method for synthesizing 6-chloro furan [3, 2-B] pyridine

A synthesis method and chlorofuran technology are applied in the synthesis field of 6-chlorofuran[3,2-B]pyridine, can solve problems such as lack of a quantitative synthesis method, achieve high yield, simple synthesis route, and cheap raw materials and reagents Effect

Inactive Publication Date: 2017-09-29
上海吉尔多肽有限公司
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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 6-chlorofuro[3,2-B]pyridine, which mainly solves the technical problem that it lacks a quantitative synthetic method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] step 1:

[0011] Add 5-chloro-3-hydroxypyridine (5.12 g, 39.7 mmol), iodine (10.1 g, 39.7 mmol), sodium carbonate (8.83 g, 83.3 mmol) and water (80 mL) into a 250 ml three-neck flask. After stirring at room temperature for 4 hours, 1 M hydrochloric acid (120 mL) was added, extracted with ethyl acetate (50 mL x 3); the organic phases were combined, washed with saturated brine (50 mL), dried over sodium sulfate, and filtered. The filtrate was spin-dried, and the crude product was recrystallized in petroleum ether to obtain a brown solid, compound 1 (9.11 g, 35.8 mmol, 90%). 1 H NMR (400 MHz, DMSO-d 6 ): 11.42 (s, 1H), 7.95 (m, 1H), 7.17 (m, 1H) ppm. LC-MS (ESI): m / z 255.72 [M+H] + ;

[0012] Step 2:

[0013] Add compound 1 (1.88 g, 6.27 mmol), triethylamine (12 mL) and 1,4-dioxane (12 mL) into a 100 mL three-neck flask. Under nitrogen protection, trimethylethynyl silicon (1.15 mL, 8.15 mmol), bistriphenylphosphine palladium dichloride (132 mg, 0.188 mmol) and cuprou...

Embodiment 2

[0016] Embodiment 2: the reaction temperature of the second step is 30° C., and the reaction time is 4 hours; the rest are the same as in Embodiment 1.

Embodiment 3

[0017] Embodiment 3: the reaction temperature of the second step is 60° C., and the reaction time is 2 hours; the rest are the same as in Embodiment 1.

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Abstract

The invention relates to a method for synthesizing 6-chlorofuro[3,2-B]pyridine. Mainly solve the technical problem of its synthetic method. The synthetic method of the present invention comprises the following steps: 5-chloro-3-hydroxypyridine reacts with iodine and sodium carbonate at room temperature to generate compound 1; compound 1 reacts with trimethylethynyl silicon to generate compound under the conditions of the scorpion coupling reaction 2; Compound 2 reacted with tetrabutylammonium fluoride at room temperature to generate target compound 3. The reaction formula is as follows: , as an expensive pharmaceutical intermediate, 6-chlorofuro[3,2-B]pyridine is widely used in the pharmaceutical industry.

Description

technical field [0001] The present invention relates to the synthesis of 6-chlorofuro[3,2-B]pyridine. Background technique [0002] 6-Chlorofuro[3,2-B]pyridine (CAS: 1142192-61-7), as an expensive pharmaceutical intermediate, is widely used in the pharmaceutical industry. So far, there is no public report about its quantitative synthesis method. Contents of the invention [0003] The purpose of the present invention is to provide a synthetic method of 6-chlorofuro[3,2-B]pyridine, which mainly solves the technical problem of lack of quantitative synthetic method. [0004] The technical scheme of the present invention is: a synthetic method of 6-chlorofuro[3,2-B]pyridine, which is characterized in that it comprises the following steps: the first step, 5-chloro-3-hydroxypyridine in water, and iodine, carbonic acid Sodium reaction, the reaction solution was acidified with 1 M hydrochloric acid to obtain compound 1; in the second step, compound 1 was mixed with 1,4-dioxane an...

Claims

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Application Information

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IPC IPC(8): C07D491/048
CPCC07D491/048
Inventor 徐红岩马敬祥
Owner 上海吉尔多肽有限公司
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