Method for producing indole or indazole compound

Abstract

The present invention provides a method for producing a nitro group-containing indole or indazole compound which is an intermediate structure required to synthesize pharmaceutically useful indole or indazole compounds, the method comprising a step for halogenating a nitro group-containing benzoic acid by adding a halogen donor, such as N-iodosuccinimide, potassium iodide (KI), iodine (I2), N-bromosuccinimide, N-chlorosuccinimide, or N-fluorobenzene-sulfonimide.

Description

technical field [0001] Cross References to Related Applications [0002] This application claims the benefit of Korean Patent Application No. 10-2019-0073017 filed with the Korean Intellectual Property Office on June 19, 2019, the disclosure of which is incorporated herein by reference in its entirety. technical field [0003] The invention relates to a method for preparing an indole or indazole compound containing a nitro group, and the compound is a necessary intermediate structure for synthesizing the indole or indazole compound for pharmaceutical use. Background technique [0004] Many research results on compounds having an indole structure as a core have been reported, and representative examples include, for example, PCT International Publication No. WO2006 / 112549 reporting that the compound has glucokinase activity, reporting that the compound is useful as an anti- PCT International Publication No. WO1995 / 007276 for tumor agents and inhibitors produced by the car...

AI Technical Summary

Problems solved by technology

[0006] Conventionally, since an ether group-containing intermediate is synthesized from a nitro-group-containing benzoic acid during the synthesis of a nitro-group-containing indole or indazole compound intermediate, there is Reaction, acetylene intermediate formation reaction and cyclization reaction are limited by low reactivity, so that the rate of side reactions is high, and in order to remove by-products generated by said side reactions, each step must be subjected to a column purification process such as using diatomaceous earth Filtration and purification

Therefore, there is a limitation that each synthesis step is not performed in situ in the same reactor when performing the column purification process, so the process efficiency becomes poor, and the column purification process is difficult to scale up, so it cannot be applied to a large-scale process.

[0007] In addition, there is a limitation that when an intermediate containing an ether group is used, it is necessary to perform a process of substituting an ether group with a carboxylic acid, so that the process steps become complicated

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