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Preparation method of 1-amino indole derivative

An aminoindole derivative and a derivative technology are applied in the field of preparation of 1-aminoindole derivatives, which can solve the problems of unfriendly environment, early preparation of substrates, harsh reaction conditions and the like, and achieve strong reaction specificity, Post-processing green, easy post-processing effect

Active Publication Date: 2017-08-29
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are many problems in these methods, such as: 1) the use of halides is not environmentally friendly; 2) the reaction conditions are harsh; 3) the substrate of the reaction needs to be prepared in advance

Method used

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  • Preparation method of 1-amino indole derivative
  • Preparation method of 1-amino indole derivative
  • Preparation method of 1-amino indole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of 1-(prop-2-imino)-2-methylindole-3-carboxylic acid ethyl ester,

[0021]

[0022] 0.2 mmol of phenylhydrazine hydrochloride, 0.3 mmol of ethyl 2-diazo-3-oxobutyrate, 0.005 mmol of dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer, 0.2 mmol of sodium acetate Add to the reaction tube, add 0.4 mmol acetone and 2 ml methanol in nitrogen atmosphere, place in an oil bath at 80 °C, react for 12 h in a nitrogen protected atmosphere, remove the heat source from the reaction, and cool to room temperature. The reaction solution was concentrated and purified by column chromatography to obtain 45 mg of the target product with a yield of 87%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 ) 8.15 (d, J=7.6Hz, 1H), 7.24-7.14 (m, 2H), 6.96 (d, J=7.9Hz, 1H), 4.40 (q, J=14.2, 7.1Hz, 2H), 2.58(s, 3H), 2.38(s, 3H), 1.76(s, 3H), 1.45(t, J=7.1Hz, 3H). 13 C NMR (100MHz, CDCl 3 )δ181.1, 166.1, 141.3, 131.9, 125.0, 121.9, 121.6, 121...

Embodiment 2

[0024] Preparation of 1-(Propan-2-imino)-2-methyl-5-fluoroindole-3-carboxylic acid ethyl ester

[0025]

[0026] 0.2 mmol of 4-fluorophenylhydrazine hydrochloride, 0.3 mmol of ethyl 2-diazo-3-oxobutyrate, 0.005 mmol of dichloro(pentamethylcyclopentadienyl) rhodium(III) dimer, acetic acid Add 0.2 mmol of sodium to the reaction tube, add 0.4 mmol of acetone and 2 ml of methanol in a nitrogen atmosphere, place in an oil bath at 80 °C, and react for 12 h in a nitrogen-protected atmosphere, remove the heat source from the reaction, and cool to room temperature. The reaction solution was concentrated and purified by column chromatography to obtain 44.1 mg of the target product with a yield of 80%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ7.80 (dd, J=9.9, 2.2Hz, 1H), 6.93 (dd, J=8.8, 2.4Hz, 1H), 6.91-6.86 (m, 1H), 4.40 (q, J=7.1Hz, 2H) ), 2.57(s, 3H), 2.40(s, 3H), 1.78(s, 3H), 1.45(t, J=7.1Hz, 3H). 13 C NMR (100MHz, CDCl 3 )δ181.5, 16...

Embodiment 3

[0028] Preparation of 1-(Propan-2-imino)-2-methyl-5-chloroindole-3-carboxylic acid ethyl ester

[0029]

[0030] 0.2 mmol of 4-chlorophenylhydrazine hydrochloride, 0.3 mmol of ethyl 2-diazo-3-oxobutyrate, 0.005 mmol of dichloro(pentamethylcyclopentadienyl) rhodium(III) dimer, acetic acid Add 0.2 mmol of sodium to the reaction tube, add 0.4 mmol of acetone and 2 ml of methanol in a nitrogen atmosphere, place in an oil bath at 80 °C, and react for 12 h in a nitrogen-protected atmosphere, remove the heat source from the reaction, and cool to room temperature. The reaction solution was concentrated and purified by column chromatography to obtain 45.1 mg of the target product with a yield of 77%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 ) 8.12 (d, J=2.0Hz, 1H), 7.13 (dd, J=8.6, 2.0Hz, 1H), 6.88 (d, J=8.6Hz, 1H), 4.41 (q, J=7.1Hz, 2H), 2.57(s, 3H), 2.40(s, 3H), 1.77(s, 3H), 1.46(t, J=7.1Hz, 3H). 13 C NMR (100MHz, CDCl 3 )δ181.6, 165.6,...

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Abstract

The invention discloses a preparation method of a 1-amino indole derivative. The method comprises the steps of mixing a phenylhydrazine hydrochloride derivative, a diazo compound, an aldehyde or ketone compound, a catalyst, alkali and an organic solvent evenly; and carrying out condensation reaction in air or nitrogen at 80-100 DEG C for 2-12h to obtain the 1-amino indole derivative. The 1-amino indole derivative which cannot be synthesized by other others can be synthesized, and the used raw materials are available, high in yield, mild in reaction condition, wide in substrate range, high in reaction specificity, and simple and green in aftertreatment.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method of a 1-aminoindole derivative. Background technique [0002] 1-Aminoindole derivatives are a class of widely used organic synthesis intermediates, which have important application value in natural products, biomedicine, and organic synthesis. Therefore, the research on the new synthesis method of 1-aminoindole has important application value and has attracted the attention of researchers in related fields. [0003] Traditional methods for synthesizing 1-aminoindole derivatives include palladium-catalyzed intramolecular condensation reaction of o-chloroarylacetaldehyde N-N-dimethylhydrazone, and palladium-catalyzed intermolecular condensation reaction of o-chlorophenylacetylene and N-N disubstituted hydrazine. However, these methods all have many problems, such as: 1) the use of halogenated compounds is not environmentally friendly; 2) the reaction ...

Claims

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Application Information

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IPC IPC(8): C07D209/42
CPCC07D209/42
Inventor 崔秀灵杨梓
Owner HUAQIAO UNIVERSITY
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