Method for aryl debromination and acylation of brominated benzazepine compound

By utilizing microchannel continuous flow technology, aminoalkylsilane compounds and alkyllithium react with amide compounds under mild conditions, solving the problems of harsh reaction conditions and low yield in the synthesis of acyl-substituted benzo[a]azine heterocyclic compounds in existing technologies, and realizing efficient, green and environmentally friendly industrial production.

WO2026044951A1 Publication Date: 2026-03-05SHANGHAI WOKAI BIOTECH
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Patent Information

Application Number
PCT/CN2024/133438
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2024-08-26
Filing Date
2024-11-21
Publication Date
2026-03-05

AI Technical Summary

Technical Problem

Existing methods for preparing acyl-substituted benzo[a]azine heterocyclic compounds involve harsh reaction conditions, cumbersome steps, and require pretreatment or post-treatment of reactants and products, making large-scale production difficult and yielding low yields.

Method used

Using microchannel continuous flow technology, aminoalkylsilane compounds are used as hydrogen-removing agents and alkyllithium compounds as debromination agents to directly synthesize acylbenzo[a]azine heterocyclic compounds in a three-step reaction under mild conditions, simplifying the post-processing.

Benefits of technology

It has achieved efficient synthesis of acylbenzo[a]azine heterocyclic compounds under mild conditions, which is suitable for large-scale industrial production. The reaction conditions are mild, the yield is high, the purity is good, and the emissions of "three wastes" are reduced, making it green and environmentally friendly.

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Abstract

The present invention relates to the field of compound synthesis, and in particular to a method for aryl debromination and acylation of a brominated benzazepine compound. The method comprises the following steps: mixing a solution containing a brominated benzazepine compound with a solution containing a dehydrogenation reagent to implement a first reaction to remove active hydrogen from an azacyclic ring, so as to obtain a first material; mixing the first material with a solution containing a debromination reagent to implement a second reaction to obtain a second material; subjecting the second material and a solution containing an amide compound to a third reaction, so that a nucleophilic substitution occurs in a substitution position of original bromine on the aryl of the brominated benzazepine compound to obtain an acylated substituent; and after the reaction is complete, quenching the resulting material and performing work-up to obtain an acyl-substituted benzazepine compound, wherein the brominated benzazepine compound is selected from one of a brominated indole compound, a brominated benzimidazole compound, a brominated indazole compound, a brominated indoline compound, and a brominated carbazole compound. The method of the present invention employs mild conditions and provides a product yield of 80% or more.
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