Preparation of condensed ring indole compounds

A technology for compounds and indoles, applied in the field of organic compound synthesis and preparation, can solve the problems of high toxicity of SnH, no industrial application value, low yield and the like, and achieve the effects of high industrial application value, convenient operation and simple process

Active Publication Date: 2008-11-12
CHINA GATEWAY PHARMA DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But this method does not 3 SnH has high toxicity and low yield, so it has no industrial application value

Method used

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  • Preparation of condensed ring indole compounds
  • Preparation of condensed ring indole compounds
  • Preparation of condensed ring indole compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] In the 250 ml three-necked bottle, a thermometer and a stirrer were installed, and the condensed ring indole carboxylic acid (R 1 =H, 0.1 mol), potassium chloride (0.1 mol), xylene (100 ml), then heated to 120° C. under reflux and stirred for 10 hours. Then the solvent was evaporated under reduced pressure, cooled to normal temperature, water (100 ml) was added, and the product was filtered and dried to obtain the product as a light yellow solid with a yield of 89% and a purity of 99.0 area% (HPLC).

Embodiment 2

[0023] In the 250 ml three-necked bottle, a thermometer and a stirrer are installed, and the condensed ring indole carboxylic acid (R 1 =5-CH 3 , 0.1mol), sodium chloride (0.12mol), toluene (100ml), and then heated to 100° C. under reflux and stirred for 15 hours. Then the solvent was evaporated under reduced pressure, cooled to normal temperature, water (110 ml) was added, and the product was filtered and dried to obtain the product as a light yellow solid with a yield of 85% and a purity of 99.5 area% (HPLC).

Embodiment 3

[0025] In the 250 ml three-necked bottle, a thermometer and a stirrer were installed, and the condensed ring indole carboxylic acid (R 1 =5-F, 0.1 mol), calcium chloride (0.2 mol), chlorobenzene (120 ml), then heated to 130° C. under reflux and stirred for 16 hours. Then the solvent was evaporated under reduced pressure, cooled to normal temperature, water (120 ml) was added, and the product was filtered and dried to obtain the product as a light yellow solid with a yield of 65% and a purity of 99.2 area% (HPLC).

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Abstract

The invention discloses a method for preparing fused ring indole type compounds as shown in formula I. The method is characterized in that: in a solvent, a fused ring indole carboxylic acid type compound as shown in formula II reacts with chloride salt which is 1-10 times the molar quantity of the compound at the temperature between 80 and 150 DEG C; (as shown in a figure) wherein R1 is H, F, Cl, Br, I, methyl or ethyl. The method can prepare the key intermediate fused ring indole type compounds of high-purity medicine (5-HT3 receptor). The method is simple in process, convenient to operate and easy to apply to large-scale industrial production, thereby having high industrial application value.

Description

technical field [0001] The invention relates to the field of synthesis and preparation of organic compounds, in particular to a preparation method of condensed ring indole compounds. Background technique [0002] In recent years, heterocyclic compounds have been widely used in drug synthesis. Among them, fused-ring indole compounds have been paid more and more attention as important intermediates of drugs (5-HT3 receptors). [0003] In the prior art, the main synthetic methods of fused ring indole compounds are: [0004] (1) I. von Wijngaarden (J. Med. Chem. 1993, 36, p3693) et al reported a synthesis method of fused ring indole compounds. Among them, the decarboxylation reaction of pyrroloquinoline carboxylic acid uses quinoline, which is more toxic, as a solvent, and the toxic and harmful CuO / Cr 2 o 3 It is a decarboxylation reagent, which makes the post-processing of the process complicated, especially the post-processing of toxic and harmful metal chromium is difficu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06
Inventor 刘国斌李原强匡通涛李文文王震孙永峰
Owner CHINA GATEWAY PHARMA DEV CO LTD
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