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Aromatic carboxylic acid trifluoroethyl ester compound and preparation method thereof

A technology for aromatic carboxylic acid trifluoroethyl ester and carboxylic acid trifluoroethyl ester, which is applied in the fields of preparing aromatic carboxylic acid trifluoroethyl ester compounds and preparing aromatic carboxylic acid trifluoroethyl ester compounds, and can solve harsh reaction conditions , high product yield, less by-products, etc., to achieve the effect of less side reactions, simple reaction operation and low production cost

Inactive Publication Date: 2018-09-07
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0014] Aiming at defects such as large excess of raw materials used in the synthesis process of existing trifluoroethyl esters, harsh reaction conditions, and scarcity of methods, the purpose of the present invention is to provide a method that does not require the use of metals or metalloids as catalysts or oxidants, and reacts A method for preparing trifluoroethyl ester compounds with mild conditions, high product yield, and few by-products. This method designs and synthesizes trifluoroethyl ester compounds with a new structure, providing a source of raw materials for drug screening and new drug synthesis

Method used

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  • Aromatic carboxylic acid trifluoroethyl ester compound and preparation method thereof
  • Aromatic carboxylic acid trifluoroethyl ester compound and preparation method thereof
  • Aromatic carboxylic acid trifluoroethyl ester compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～17

[0035] The following implementations 1-17 are prepared according to the following synthetic route, and compounds 1-17 can be prepared:

[0036]

[0037] The specific operation is: dissolve the aromatic carboxylic acid substrate (0.5mmol, 1equiv) in 1,1,1,3,3,3-hexafluoro-2-propanol (3ml), add dropwise tert-butyl nitrite ( 150μL, 1.25mmol, 2.5equiv) and 2,2,2-trifluoroethylamine (100μL, 1.25mmol, 2.5equiv), stirred at room temperature for 1-10h, the solution in the reaction system was spin-dried under reduced pressure, and the residue Purify by column chromatography to obtain aromatic carboxylic acid trifluoroethyl ester compounds.

[0038] The pharmaceutical reagents used in the examples of the present invention were purchased from Anaiji Chemical Company.

[0039] Structural characterization of the compound:

[0040] Compound structures were determined by nuclear magnetic resonance (NMR) or mass spectroscopy (MS). The mensuration of NMR is to use BrukerAVANCE-400 or Var...

Embodiment 1

[0046] Benzoic acid (61 mg, 0.5 mmol, 1 equiv) was dissolved in 1,1,1,3,3,3-hexafluoro-2-propanol (3 ml); tert-butyl nitrite (150 μL, 1.25 mmol, 2.5 equiv ) and trifluoroethylamine (100 μL, 1.25 mmol, 2.5 equiv) were stirred evenly, and reacted at room temperature for 10 hours. After the reaction was complete, spin-dried under reduced pressure, and separated by silica gel flash column chromatography to obtain the target compound 1.

[0047] Substrate: Benzoic acid

[0048] product:

[0049] Compound 1: colorless oil (87mg, 85% yield); 1 H NMR (400MHz, CDCl 3 )δ8.08–7.94(m,2H),7.62–7.50(m,1H),7.40(t,J=7.8Hz,2H),4.62(q,J=8.4Hz,2H); 13 C NMR (100MHz, CDCl 3 )δ163.9, 132.9, 129.0, 127.6, 127.3, 122.1 (q, J = 277.2Hz), 59.8 (q, J = 36.7Hz); 19 FNMR (376MHz, CDCl 3 )δ-73.68(t, J=8.6Hz); 19 F { 1 H}NMR (376MHz, CDCl 3 )δ-73.68.

Embodiment 2

[0051] Dissolve o-iodobenzoic acid (124 mg, 0.5 mmol, 1 equiv) in 1,1,1,3,3,3-hexafluoro-2-propanol (3 ml); add tert-butyl nitrite (150 μL, 1.25 mmol, 2.5 equiv) and trifluoroethylamine (100 μL, 1.25 mmol, 2.5 equiv) were stirred evenly, and reacted at room temperature for 10 hours. After the reaction was complete, spin-dried under reduced pressure, and separated by silica gel flash column chromatography to obtain the target compound 2.

[0052] Substrate: o-iodobenzoic acid

[0053] product:

[0054] Compound 2: colorless oil (154mg, 83% yield); 1 H NMR (400MHz, CDCl 3 )δ7.96(dd, J=8.0, 1.2Hz, 1H), 7.82(dd, J=7.8, 1.7Hz, 1H), 7.36(td, J=7.6, 1.2Hz, 1H), 7.13(td, J =7.7,1.7Hz, 1H), 4.63(q, J=8.3Hz, 2H); 13 C NMR (100MHz, CDCl 3 )δ163.4, 140.8, 132.5, 131.8, 130.6, 127.1, 122.0 (q, J = 277.3Hz), 93.6, 60.1 (q, J = 36.9Hz); 19 F NMR (376MHz, CDCl 3 )δ-73.31 (t, J=8.3Hz); 19 F{ 1 H}NMR (376MHz, CDCl 3 )δ-73.31; HRMS (ESI) m / z calcdfor C 9 h 7 f 3 IO 2 + ,[M+H] +...

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Abstract

The invention discloses an aromatic carboxylic acid trifluoroethyl ester compound and a preparation method thereof. The invention provides the aromatic carboxylic acid trifluorethylmethyl ester compound and the preparation method thereof. The preparation method comprises the following step of performing reaction on aromatic carboxylic acid, t-butyl nitrite and 2,2,2-trifluoroethylamine with a one-pot method to obtain the carboxylic acid trifluoroethyl ester compound. The method is simple to operate, mild in reaction condition, low in cost, less in byproduct and high in yield, is capable of obtaining the aromatic carboxylic acid trifluoroethyl ester compound without being limited by a substrate so as to establish an aromatic carboxylic acid trifluoroethyl ester compound library and providesa raw material source to drug screening and new drug synthesis.

Description

technical field [0001] The invention relates to a method for preparing aromatic carboxylic acid trifluoroethyl esters by a one-step one-pot method, in particular to the preparation of aromatic carboxylic acid trifluoroethyl by using aromatic carboxylic acid and 2,2,2-trifluoroethylamine as raw materials The method for ester compounds belongs to the technical field of fluorine chemistry and pharmaceutical intermediate synthesis. Background technique [0002] In recent years, 20% of drugs and 30% of pesticides on the market contain at least one fluorine atom. Many fluorine-containing compounds have special properties due to the introduction of fluorine atoms, and have attracted more and more attention from scientists. As a class of compounds with fluorine atoms introduced, trifluorodiazoethane has the characteristics of high-efficiency reaction rate, excellent selectivity, product specificity, no need for catalysts, and no toxic by-products. It is widely used in natural produ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/78C07C69/76C07C69/84C07C69/92C07C69/82C07C69/618C07C69/612C07C69/65C07C67/00C07C201/12C07C253/30C07C205/57C07C255/57C07D213/79C07D333/38C07D209/42
CPCC07C69/78C07C69/612C07C69/618C07C69/65C07C69/76C07C69/82C07C69/84C07C69/92C07C205/57C07C255/57C07D209/42C07D213/79C07D333/38
Inventor 胡祥国高玉彭山青
Owner JIANGXI NORMAL UNIV
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