5-bromo-6-chloro-3-indolyl caprylate synthesis method

Abstract

The invention discloses a 5-bromo-6-chloro-3-indolyl caprylate synthesis method, which is characterized in that 4-chloro-2-aminobenzoic acid and N-bromosuccinimide are subjected to a bromination reaction to obtain 5-bromo-4-chloro-2-aminobenzoic acid, 5-bromo-4-chloro-2-aminobenzoic acid and sodium chloroacetate are subjected to a nucleophilic substitution reaction to obtain N-(4-bromo-5-chloro-2-carboxy)phenylglycine, N-(4-bromo-5-chloro-2-carboxy)phenylglycine is subjected to a cyclization decarboxylation reaction to obtain 1-acetyl-5-bromo-6-chloro-3-indole ethyl ester, and 1-acetyl-5-bromo-6-chloro-3-indole ethyl ester and octanoyl chloride are subjected to a selective esterification reaction to obtain 5-bromo-6-chloro-3-indolyl caprylate. According to the present invention, the 5-bromo-6-chloro-3-indolyl caprylate synthesis method has advantages of high efficiency, safety, environmental protection and relatively high total reaction yield, and can be used for the large-scale synthesis of 5-bromo-6-chloro-3-indolyl caprylate.

Description

[0001] Technical field: [0002] The invention belongs to the technical field of organic synthesis and biological analysis and detection, in particular to a synthetic method of 5-bromo-6-chloro-3-indooctyl ester. [0003] Background technique: [0004] Holt et al. (Proc.R.Soc.B, 1958,148,481-494) have reported that by using halogenated aniline, anthranilic acid, N-(2-carboxy) phenylglycine substituent three compounds as starting A series of different substituted 1-acetyl-3-indole ethyl esters were synthesized through different routes, and then different substituted acetate chromogenic substrates were further synthesized. Wherein, the synthesis of 5-bromo-6-chloro-3-indole ethyl ester involves: N-(5-chloro-2-carboxy) phenylglycine takes place in the aromatic ring bromination reaction under liquid bromine / acetic acid conditions (producing Yield is 78%), the N-(4-bromo-5-chloro-2-carboxy) phenylglycine that obtains takes place cyclodecarboxylation reaction (productivity is 42%) u...

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Problems solved by technology

[0011] The following problems exist in the above-mentioned synthetic research: the synthetic route of 5-bromo-6-chloro-3-indooctyl and its specific preparation process have not been reported; for the synthesis of intermediates, during the bromination reaction, highly toxic liquid bromine is used As brominated reagents, solvents such as acetic acid and chlorosulfonic acid are difficult to recycle, which can easily lead to more pollutants; the total yield of some other reaction steps or intermediate reaction routes is low, etc.

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