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Heterocycle-containing trifluoromethyl ketone compound and preparation method thereof

A technology for trifluoromethyl ketones and heterocyclic compounds, which is applied in the field of heterocyclic-containing trifluoromethyl ketone compounds and its preparation, can solve problems such as no further research and no preparation of trifluoromethyl ketone compounds, and achieve Wide applicability, low cost, and high productivity

Active Publication Date: 2015-05-13
浙江药领医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of reaction has not been further studied, and there is no general method for the preparation of pyridine and related heterocyclic trifluoromethyl ketone compounds with substituents.

Method used

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  • Heterocycle-containing trifluoromethyl ketone compound and preparation method thereof
  • Heterocycle-containing trifluoromethyl ketone compound and preparation method thereof
  • Heterocycle-containing trifluoromethyl ketone compound and preparation method thereof

Examples

Experimental program
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Embodiment 1

[0029] The heterocyclic-containing trifluoromethyl ketone compound in this example is 2-trifluoroacetyl-5-bromopyridine. with R 1 , R 2 , R 3 The heterocyclic compound is 2,5-dibromopyridine, where R 1 for hydrogen, R 2 is bromine(5), R 3 is bromo(2), and the heterocycle type of the heterocyclic compound is pyridine.

[0030] The preparation method of the heterocyclic-containing trifluoromethyl ketone compound of the present embodiment comprises the following steps:

[0031] 1) Dissolve 10mmol of 2,5-dibromopyridine in 20ml of toluene, slowly add organolithium reagent (n-BuLi, 11mmol) dropwise under nitrogen protection, and react at -78°C for 2h to obtain organolithium intermediate body;

[0032] 2) Slowly add 15 mmol of N-trifluoroacetylmorpholine dropwise to the organolithium intermediate obtained in step 1), react at -78°C for 2 hours, raise the temperature to room temperature naturally, stir overnight, and then use at 20°C 10ml of water is used as a quenching agent...

experiment example

[0054] This experimental example detected the product yield of the preparation method of the trifluoromethyl ketone compound of Examples 1-26, and carried out NMR characterization to the product obtained by the preparation method of the trifluoromethyl ketone compound of Examples 1-26, the result As shown in Table 5.

[0055] Table 5 Product yield and NMR characterization of the preparation methods of trifluoromethyl ketone compounds in Examples 1-26.

[0056]

[0057]

[0058]

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PUM

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Abstract

The invention discloses a heterocycle-containing trifluoromethyl ketone compound and a preparation method thereof. The trifluoromethyl ketone compound is a heterocyclic compound having R1, R2 and trifluoroacetyl. The heterocycle of the heterocyclic compound is of pyridine, pyrimidine, pyridazine, benzothiophene or benzofuran. The preparation method includes: 1) dissolving the heterocyclic compound containing R1, R2 and R3 in a solvent, adding an organolithium reagent in the presence of an inert gas, and reacting at -78 to -10 DEG C to get an organolithium intermediate; and 2) adding N-trifluoroacetylmorpholine to the organolithium intermediate in the step 1), reacting at -78-0 DEG C for a period, quenching the reaction by a quencher, and separating the reaction product. The heterocycle-containing trifluoromethyl ketone compound can be used as an enzyme inhibitor. The preparation method of the present invention can synthesize the heterocycle-containing trifluoromethyl ketone compound in one step, is simple to operate and high in yield, and has a wide application range.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a heterocyclic-containing trifluoromethyl ketone compound and a preparation method thereof. Background technique [0002] Trifluoromethyl ketones have attracted increasing attention as potent enzyme inhibitors. At present, there are many methods to directly introduce trifluoroacetyl groups into organic molecules, such as: 1) Friedel-Crafts acylation reaction; 2) reaction of organometallic reagents with trifluoroacetic acid derivatives; 3) carboxylate and TMS-CF 3 reaction; 4) Cd(CF 3 ) 2 / RCOCl and AgCF 3 / RCOCl system; 5) Palladium-catalyzed cross-coupling reaction. However, the most traditional and useful method is the reaction of organometallic reagents with trifluoroacetic acid derivatives. [0003] In the prior art, in 1956, Dishart and Levine reported for the first time the one-step synthesis of trifluoromethyl ketone compound with Grigna...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/61C07D213/75C07D239/30C07D237/12C07D237/14C07D333/56C07D307/80
Inventor 吴豫生邹大鹏李敬亚郭瑞云高剑昕孙春霞牛成山
Owner 浙江药领医药科技有限公司
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