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Industrial preparation method of heterocyclic derivative

A derivative and industrial technology, applied in the field of industrial preparation of heterocyclic derivatives, can solve the problems of lengthy synthetic routes, lower production efficiency, and higher production costs, and achieve the effects of increased operational difficulties, increased costs, and convenient post-processing

Inactive Publication Date: 2017-04-05
王志训
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, in the existing technology, the synthesis of this type of compound often has problems such as lengthy synthetic routes, complicated steps, complicated by-products, and difficult separation, which in turn reduces production efficiency and increases production costs.

Method used

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  • Industrial preparation method of heterocyclic derivative
  • Industrial preparation method of heterocyclic derivative
  • Industrial preparation method of heterocyclic derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059]

[0060] Slowly add 700g of furan (tetrahydrofuran dissolved in 1000ml) dropwise into 230g of metal sodium sand (an electron transfer agent such as α-methylstyrene can also be added during the reaction), react at room temperature for 2-4 hours, and Add 1500g diethyl oxalate dropwise while stirring, react at room temperature for 2 hours, filter, neutralize the reaction solution to pH=6.5-7.5, extract twice with 500ml ethyl acetate, take the organic layer, evaporate the solvent to obtain 1519g product, the product The final ester compound can be obtained by reduction.

Embodiment 2

[0062]

[0063] Slowly add 900g of p-picoline dropwise to 400g of potassium metal, reflux for 1 hour, cool to room temperature, add 1400g of diethyl oxalate dropwise while stirring, reflux for 4 hours, heat filter, and neutralize the reaction solution to pH =6.5-7.5, extracted twice with 500ml ethyl acetate, took the organic layer, evaporated the solvent to obtain 1732g product.

[0064] In this reaction, the N on the pyridine ring can also be considered to be protected before proceeding.

Embodiment 3

[0066]

[0067] Slowly add 900g of 2-methylfuran dropwise to 1500g of tert-butyllithium, reflux for 4 hours, cool to room temperature, add 1460g of diethyl oxalate dropwise while stirring, reflux for 1 hour, and obtain 1701g of product by rectification .

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Abstract

The invention provides an industrial preparation method of a heterocyclic derivative. The method is characterized in that a compound B reacts with diethyl oxalate to generate a target compound C, wherein structures of the compound B and the target compound C are shown in the description. The preparation method is simple and is different from the prior art which is complicated in production manner and strict in production conditions. According to the preparation method, the target product can be synthesized in one step. Since the production process and synthetic routes are optimized in the method, side reactions are less, the postprocessing becomes convenient, and the production condition is mild in the production process, and the method is suitable for industrial production manner.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to an industrial preparation method of heterocyclic derivatives. Background technique [0002] Heterocyclic aromatic derivatives are widely used, such as: furan derivatives, nitrogen-containing seven-membered ring derivatives, etc. are widely used in various fields such as electronics, biology, medicine, and materials. For example, furan ammonium salt is an important intermediate for the preparation of antibiotics. Many heterocyclic derivatives can be used to treat various cancers: such as bladder cancer, breast cancer, colon cancer, kidney cancer, liver cancer, lung cancer (including small cell lung cancer), esophageal cancer, gallbladder cancer, ovarian cancer, pancreatic cancer, gastric cancer, Cancer of the cervix, thyroid, prostate, and skin (including squamous cell carcinoma); hematopoietic neoplasms of the lymphoid lineage, including leukemia, acute lymphoblastic leukemia, a...

Claims

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Application Information

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IPC IPC(8): C07D307/54C07D213/55C07D337/04
CPCC07D307/54C07D213/55C07D337/04
Inventor 王志训
Owner 王志训
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