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Solvent-free synthesis method of 1-(2-pyridyl)indoline derivative

A synthetic method, indoline technology, applied in the direction of organic chemistry, etc., to achieve the effect of mild conditions, good atom economy, and convenient post-processing

Inactive Publication Date: 2019-01-25
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] There are obvious limitations in previous reports. Therefore, it is necessary to develop a simple and inexpensive synthetic process to synthesize the target product in one step while ensuring the tolerance of the functional group of the reaction substrate, while avoiding the use of the above-mentioned reports. Experimental consumables and reaction devices such as expensive ligands, catalysts, transition metal complexes, and microwave reactors are already a problem worth studying

Method used

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  • Solvent-free synthesis method of 1-(2-pyridyl)indoline derivative
  • Solvent-free synthesis method of 1-(2-pyridyl)indoline derivative
  • Solvent-free synthesis method of 1-(2-pyridyl)indoline derivative

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preparation example Construction

[0028] This synthetic method specifically comprises the following steps:

[0029] Step 1: Add indoline or indoline derivatives and pyridine derivatives into corresponding round bottom flasks; the pyridine derivatives are 2-chloropyridine derivatives or 2-bromopyridine derivatives.

[0030] Step 2: The ratio of the amount of substances between the indoline derivatives and the 2-chloropyridine derivatives is 1:1 to 1:1.5; the ratio of the amounts of the substances between the indoline derivatives and the 2-bromopyridine derivatives is 1 : 1~1: 1.5;

[0031] Step 3: Stir directly in the air, mix evenly at room temperature, then turn on the heating, set the temperature at 80-100°C, stop the reaction after the system solidifies, and cool to room temperature;

[0032] Step 4: Add a certain amount of saturated NaHCO to the system 3 Solution, dissolve the solid, then add an appropriate amount of ethyl acetate solution, shake, separate the liquid, extract the aqueous phase with ethyl...

Embodiment 1

[0037]

[0038] A kind of synthesis of 1-(2-pyridyl) indoline:

[0039] ① Add 1.19g of indoline and 1.73g of 2-bromopyridine into a 50mL round bottom flask, and the ratio of the substances is 1: 1.1;

[0040] ② Stir directly in the air, mix evenly at room temperature, then heat to 100°C, the system solidifies after 2 minutes, stops the reaction, and cools to room temperature;

[0041] ③Add 50mL saturated NaHCO to the system 3 solution, dissolve the solid, then add 50 mL of ethyl acetate solution, shake, separate the liquids, extract the aqueous phase with ethyl acetate three times, 30 mL each time, combine the organic phases, and concentrate with a rotary evaporator;

[0042] ④: Dissolve the concentrated solution in 15mL ethanol, reflux at 80°C for 5min, cool, precipitate a light yellow solid, filter, rinse with water, and dry under vacuum to obtain the target product with a purity of 97% (NMR analysis) and a yield of 93%. .

[0043] The compound obtained is a known comp...

Embodiment 2

[0046]

[0047] A kind of synthesis of 2-methyl-1-(2-pyridyl)indoline:

[0048] ①Add 1.33g 2-methylindoline and 1.41g 2-chloropyridine into a 50mL round bottom flask, the ratio of the substances is 1:1.25;

[0049] ②Stir directly in the air, mix evenly at room temperature, then heat to 90°C, the system solidifies after 24 minutes, stops the reaction, and cools to room temperature;

[0050] ③Add 50mL saturated NaHCO to the system 3 solution, dissolve the solid, then add 50 mL of ethyl acetate solution, shake, separate the liquids, extract the aqueous phase with ethyl acetate three times, 30 mL each time, combine the organic phases, and concentrate with a rotary evaporator;

[0051] ④: Dissolve the concentrated solution in 15mL ethanol, reflux at 80°C for 5min, cool, precipitate a light yellow solid, filter, rinse with water, and dry under vacuum to obtain the target product with a purity of 96% (NMR analysis) and a yield of 81%. .

[0052] The compound obtained is a known...

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Abstract

A solvent-free synthesis method of a 1-(2-pyridyl)indoline compound is provided. The method includes adding an indoline derivative and a pyridine derivative to a container, stirring uniformly, curingat 80-100 DEG C and then cooling to the room temperature; then adding a NaHCO3 solution to dissolve the solid, adding ethyl acetate, shaking, separating and concentrating; dissolving a concentrated solution in ethanol, refluxing for 5-20 min, cooling, filtering and drying to obtain the 1-(2-pyridyl)indoline compound. The method has the advantages of being simple in operation, low in cost, convenient to post treat, easy to amplify and good in atomic economy.

Description

technical field [0001] The invention relates to a solvent-free synthesis method of 1-(2-pyridyl)indoline. Background technique [0002] 1-(2-pyridyl)indoline compounds are important intermediates for preparing other 7-substituted indolines, and are also important raw materials for the synthesis of dyes and drugs. In this structure, pyridine can act as a directing group to coordinate with transition metals regioselectively, guiding the metal to activate the C–H bond at the 7-position of the indoline substrate. A variety of corresponding reactions have been realized so far, including alkylation (W.Ai et.al., Chem.Eur.J.2014,20,17653.), allylation (G.S.Kumaret.al., Org.Lett.2016,18,1112.), alkenylation (X.-F.Yang et.al., Chem.Commun.2015,51,2532.), alkynylation (Y.Wu et.al. , J.Org.Chem.2015,80,1946; X.Zhou et.al., J.Org.Chem.2016,81,4869.), acylation (N.Chatani et.al., J.Org. Chem.2002,67,7557; H.Jo et.al.,Tetrahedron 2017,73,1725.), acyl methylation (T.M.Ha et.al.,Org.Lett...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 焦林郁张泽殷晓美洪乾宁资慧马晓迅李卓孙鸣
Owner NORTHWEST UNIV(CN)
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