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Method of synthesizing 2-vinyl indole derivative

A technology of ethylene indole derivatives and ethylene, which is applied in the field of synthesizing 2-vinylindole derivatives, can solve the problems of unstable yield, inability to synthesize 2-vinylindole derivatives, large limitations, etc., and achieve reaction Simple steps, easy operation, and highly responsive effects

Active Publication Date: 2017-07-07
JIANGHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But, the yield of above-mentioned several methods is unstable, and is subjected to the limitation of raw material bigger, can't use the simplest indole as raw material synthesis 2-vinylindole derivatives

Method used

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  • Method of synthesizing 2-vinyl indole derivative
  • Method of synthesizing 2-vinyl indole derivative
  • Method of synthesizing 2-vinyl indole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] In this example: R 1 is hydrogen; R 2 For methyl.

[0038] Step: In a 10mL reaction flask, add compound I-1 (0.2mmol), potassium vinyl trifluoroborate (0.3mmol), AgOAc (0.3mmol), [RhCp*Cl 2 ] 2(2mol%), methanol (0.5mL), trifluoroethanol (0.5mL), the mixture was reacted at 40°C, and the reaction was detected by TLC (thin layer chromatography) until the reaction was complete. Post-processing purification: cooling to room temperature, concentrated under pressure. The crude product was separated and purified by silica gel column chromatography, and the mobile phase was a mixed solvent of V (petroleum ether): V (ethyl acetate) = 5:1 to obtain a pure product, a white solid, with a yield of 82%.

[0039] Compound II-1 was tested:

[0040] The melting point is 99-100°C;

[0041] 1 H NMR (400MHz, CDCl 3 )δ8.77(d, J=4.8Hz, 2H), 8.27(d, J=7.9Hz, 1H), 7.57(d, J=7.2Hz, 1H), 7.31-7.21(m, 2H), 7.11- 7.02(m,2H),5.50-5.38(m,2H),2.44(s,3H).

[0042] 13 C NMR (100MH...

Embodiment 2

[0045]

[0046] In this example: R 1 is methyl; R 2 For methyl.

[0047] Step: In a 10mL reaction flask, add compound I-2 (0.2mmol), potassium vinyltrifluoroborate (0.3mmol), AgOAc (0.3mmol), [RhCp*Cl 2 ] 2 (2mol%), methanol (0.5mL), trifluoroethanol (0.5mL), the mixture was placed at 40°C for reaction, and TLC (thin layer chromatography) detected that the reaction was complete. Post-processing purification: cooling to room temperature, concentrated under pressure. The crude product was separated and purified by silica gel column chromatography, and the mobile phase was a mixed solvent of V (petroleum ether): V (ethyl acetate) = 5:1 to obtain a pure product, a white solid, with a yield of 72%.

[0048] Compound II-2 was tested:

[0049] The melting point is 116-117°C;

[0050] 1 H NMR (400MHz, CDCl 3 )δ8.77(d,J=4.8Hz,2H),8.02(d,J=8.4Hz,1H),7.13–7.09(m,2H),6.97–6.90(m,2H),5.45(dd,J =11.5,1.6Hz,1H),5.29(dd,J=17.7,1.6Hz,1H),2.76(s,3H),2.62(s,3H).

[0051] 13 C NMR (...

Embodiment 3

[0054]

[0055] In this example: R 1 is benzyloxy; R 2 methyl.

[0056] Step: In a 10mL reaction flask, add compound I-3 (0.2mmol), potassium vinyltrifluoroborate (0.3mmol), AgOAc (0.3mmol), [RhCp*Cl 2 ] 2 (2mol%), methanol (0.5mL), trifluoroethanol (0.5mL), the mixture was placed at 40°C for reaction, and TLC (thin layer chromatography) detected that the reaction was complete. Post-processing purification: cooling to room temperature, concentrated under pressure. The crude product was separated and purified by silica gel column chromatography, and the mobile phase was a mixed solvent of V (petroleum ether): V (ethyl acetate) = 5:1 to obtain a pure product, a white solid, with a yield of 61%.

[0057] Compound II-3 was tested:

[0058] The melting point is 107-108°C;

[0059] 1 H NMR (400MHz, CDCl 3 )δ8.77(d, J=4.8Hz, 2H), 7.80(d, J=8.4Hz, 1H), 7.51(d, J=7.3Hz, 2H), 7.40(t, J=7.4Hz, 2H) ,7.34–7.31(m,1H),7.17–7.08(m,2H),6.93(dd,J=17.7,11.5Hz,1H),6.68(d,J=7.9Hz,1H),5...

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Abstract

The invention discloses a method of synthesizing a 2-vinyl indole derivative. The synthesis method comprises the following steps: mixing an indole derivative, vinyl trifluoro boric acid ester and silver acetate under the action of a rhodium catalyst, heating the mixture in a first solvent and air to 30-50 DEG C, and carrying out vinylation reaction to obtain the 2-vinyl indole derivative. According to the method, by selecting different substituent groups, different 2-vinyl indole derivatives can be obtained. The method does not need complex raw materials, expands a selection range of the raw materials and saves the cost. In addition, alkenyl indole without a substituent group at a terminal can be obtained by using the method provided by the invention, the reactivity is strong, and the 2-vinyl indole derivative with a terminal alkene structure can be further modified according to the needs. Meanwhile, the method can perform synthesis through one-step reaction, is simple in reaction steps, mild in reaction conditions and low in cost, can be performed in air, is liable to operate and has very strong practicability.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing 2-vinylindole derivatives. Background technique [0002] Compounds with alkenyl structures are important structural units in many natural products and drug molecules. Among these alkenyl compounds, indole and its derivatives with alkenyl structure are abundantly present in the backbones of many drug molecules and biologically active substances, and are widely used in the fields of medicinal chemistry and biochemistry. For example: Prenostodione, a natural product extracted from Nostoc cyanobacteria in 2001, has a strong ultraviolet absorption effect. Hexaloblnes, isolated from Pseudocladona cyanobacteria, are a natural pigment. In 2009, Flinderoles C, a natural substance extracted from plants of the genus Giulia, has obvious antimalarial activity and has the possibility of clinical application. In addition, alkenylindole derivatives are often used as ...

Claims

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Application Information

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IPC IPC(8): C07D403/04
Inventor 王亮张玉敏郭艳华彭望明
Owner JIANGHAN UNIVERSITY
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