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2-perfluoroalkyl indole derivative and synthesis method thereof

A technology of perfluoroalkyl indole derivatives and perfluoroalkyl, applied in organic chemistry and other fields, can solve problems such as inability to reflect diversity and cumbersome steps, and achieve unique chemical stability, physiological stability, and regioselectivity High, extended selectivity effect

Active Publication Date: 2015-09-09
SHANGHAI MACKLIN BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Summarizing the synthesis methods so far, it is not difficult to find that in the previous methods of synthesizing indole, there are certain limitations in terms of substrates, which cannot reflect diversity; secondly, other metals are often used as oxidants in transition metal catalysis , unlike oxygen, which is green and environmentally friendly; for the introduction of trifluoromethyl, the distribution reaction will be selected, which makes the steps cumbersome. Therefore, we propose a green and sustainable synthesis method with atom economy, readily available raw materials , to synthesize a series of 2-perfluoroalkylindole derivatives

Method used

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  • 2-perfluoroalkyl indole derivative and synthesis method thereof
  • 2-perfluoroalkyl indole derivative and synthesis method thereof
  • 2-perfluoroalkyl indole derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: 2-trifluoromethyl-1 H - the preparation of indole-3-carboxylic acid methyl ester, the structure of this compound is:

[0021]

[0022] Molecular formula: C 11 h 8 f 3 NO 2

[0023] Chinese name: 2-trifluoromethyl-1 H -Methyl indole-3-carboxylate

[0024] English name: methyl 2-(trifluoromethyl)-1 H -indole-3-carboxylate

[0025] Molecular weight: 243.05

[0026] Melting point: 135.6°C-136.5°C

[0027] Appearance: white solid

[0028] Proton NMR spectrum (500MHz, CDCl 3, Internal standard: TMS): 3.99 (s, 3H, OCH3), 7.32-7.35 (m, 1H, ArH), 7.37-7.40 (m, 1H, ArH), 7.48 (d, J = 8.1 Hz, 1H, ArH) , 8.26 (d, J = 8.1 Hz, 1H, ArH), 9.29 (br s, 1H, NH) ppm;

[0029] NMR fluorine spectrum (470MHz, CDCl 3 , internal standard: C 6 f 6 ): -59.85 (s, CF 3 ) ppm.

Embodiment 2

[0030] Example 2: 5-methoxy-2-trifluoromethyl-1 H - the preparation of indole-3-carboxylic acid methyl ester, the structure of this compound is:

[0031]

[0032] Molecular formula: C 12 h 10 f 3 NO 3

[0033] Chinese name: 5-methoxy-2-trifluoromethyl-1 H -Methyl indole-3-carboxylate

[0034] English name: methyl 5-methoxy-2-(trifluoromethyl)-1 H -indole-3-carboxylate

[0035] Molecular weight: 273.06

[0036] Melting point: 157.4°C-158.3°C

[0037] Appearance: white solid

[0038] Proton NMR spectrum (500MHz, CDCl 3, Internal standard: TMS): 3.87 (s, 3H), 3.97 (s, 3H), 7.01-7.03 (m, 1H), 7.35 (d, J = 9.0 Hz, 1H), 7.68 (d, J = 2.0 Hz, 1H), 9.28 (br s, 1H) ppm;

[0039] NMR fluorine spectrum (470MHz, CDCl 3 , internal standard: C 6 f 6 ): -59.86 (s, CF 3 ) ppm.

[0040] (1) A 2-perfluoroalkylindole derivative, characterized in that the structure of the compound is:

[0041]

[0042] 5-Chloro-2-trifluoromethyl-1 H -Methyl indole-3-carboxylate

[0043]...

example 1

[0367] Example 1: Preparation of 2-trifluoromethyl-1H-indole-3-carboxylic acid methyl ester

[0368] Add aniline (46.5 mg, 0.5 mmol), Pd 2 (dba) 3 (0.05g, 10 mol%), NaHCO 3 (12.5 mg, 30 mol%), pivalic acid 0.44g and a stirring magnet, after replacing oxygen, add N,N-dimethylacetamide 2 ml and methyl trifluoromethylynoate (91.2 mg, 0.6 mmol ). Stirring at 120°C for 12h, after the completion of the reaction by TLC, column chromatography gave a white solid which was 2-trifluoromethyl-1 H - methyl indole-3-carboxylate.

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Abstract

The invention relates to a 2-perfluoroalkyl indole derivative and a synthesis method thereof. The structure of the compound is represented in the specification, wherein RF represents perfluoroalkyl groups from C1 to C3. According to the method, a phenylamine derivative which is easy to obtain and perfluoroalkyl acetylenic acid ester synthesized with a mature method are taken as raw materials, and the perfluoroalkyl indole containing derivative is synthesized through Michael addition and C-H activation under certain conditions; compared with traditional modes for synthesizing like products, the method adopts phenylamine and alkynes as starting materials, so that substrate selectivity can be greatly expanded; moreover, according to the method, a conventional oxidizing agent is abandoned in an oxidation process, oxygen is taken as the oxidizing agent, and the concepts of green and sustainable chemistry are represented; the regioselectivity is high, and the yield is good. Therefore, the effective novel method for synthesizing the 2-perfluoroalkyl indole derivative is provided.

Description

technical field [0001] The invention relates to a 2-perfluoroalkyl indole derivative and a synthesis method thereof. Background technique [0002] Indole compounds are important structural substances commonly found in natural compounds, pharmaceutical intermediates and polymer functional materials, and are widely used in the fields of medicine, pesticides, dyes and spices. Therefore, chemists have been working on exploring how to better synthesize indole compounds. So far, a large number of indole ring synthesis methods have been reported, and the classic indole synthesis methods include Fiseher indole synthesis method, Bartoli indole synthesis method, Nenitzescu indole synthesis method, Kihara indole synthesis method, etc. In recent years, the method of directly constructing indole compounds by C-H activation through transition metal catalysis has become a hot research object. [0003] In the design of many new drugs, the introduction of trifluoromethyl functional groups ...

Claims

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Application Information

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IPC IPC(8): C07D209/42C07D209/60
CPCC07D209/42C07D209/60
Inventor 沈丹丹韩靖陈杰张慧曹卫国
Owner SHANGHAI MACKLIN BIOCHEM TECH
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