CN110003227B - Synthetic method of 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine - Google Patents
Synthetic method of 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine Download PDFInfo
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Abstract
The invention discloses a synthesis method of 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine, which comprises the steps of constructing a carbon-oxygen bond through nucleophilic substitution reaction of 2-chloro-3-nitro-6-methylpyridine and guaiacol under an alkaline condition, and reducing nitro groups by hydrazine hydrate under the catalysis of palladium-carbon to generate corresponding arylamine. The arylamine is subjected to ring closure under the action of isoamyl nitrite to synthesize the 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine. The method does not need to use expensive 2-amino-3-bromo-6-methylpyridine and 2, 3-dimethoxyphenylboronic acid as raw materials, and has obvious cost advantage; meanwhile, the first two steps of the method adopt nucleophilic substitution reaction and diazotization reaction which are simple to operate, so that Suzuki coupling reaction with higher operation requirement and corresponding noble metal palladium catalyst are avoided. The method has the advantages of high reaction yield, low production cost, simple post-treatment, high product purity and suitability for process amplification.
Description
Technical Field
The invention belongs to the technical field of synthesis of organic electroluminescent material intermediates, and particularly relates to a synthesis method of 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine.
Background
In recent years, organic photoelectric materials are increasingly popular, and first, the cost of raw materials of the organic photoelectric materials is lower than that of inorganic materials, so that the organic photoelectric materials have remarkable cost advantage; second, the inherent properties of organic materials, such as flexibility, make them applicable to the preparation of flexible materials. The organic photoelectric material comprises an organic light-emitting diode, an organic photoelectric transistor, an organic photovoltaic cell, an organic photodetector and the like, wherein the organic light-emitting diode (OLED for short) shows the characteristics remarkably superior to the traditional light-emitting material; in addition, the light emitting wavelength of the organic emission layer can be effectively adjusted by adding an appropriate dopant.
OLED materials fall into two broad categories: organic electroluminescent luminescent materials and organic electrophosphorescent luminescent materials. Early OLEDs were singlet fluorescent emitting, which is relaxation emitting by an electroluminescent singlet exciton through a light emitting mechanism, and the generation ratio of triplet excitons to singlet excitons in organic electroluminescence was 3: 1. the organic metal complex can be used as a phosphorescent emitter to realize the energy efficiency which is four times that of a fluorescent emitter.
The organic electrophosphorescent material shows stable physicochemical properties, lower biochemical temperature and higher saturated color CIE value, and is widely applied to various consumer goods and production and scientific research fields, such as computer displays, flat panel displays, medical displays, televisions, billboards, illumination and the like; and the device can also be used for internal or external illumination and signal transmission, such as laser screens, full-transparent display screens, wide-angle holographic display screens, flexible foldable display screens, laser printers, mobile phones, palm computers, notebook computers, tablet computers, digital cameras, video cameras, viewfinders, micro-displays and large-area display screens of vehicles, screens, theaters or gymnasiums. The organic electrophosphorescent material can also be used for other photoelectric devices, such as organic solar cells, organic photodetectors, organic transistors and the like.
The OLED phosphorescent emitter material is usually a complex of iridium and platinum, tris (2-phenylpyridine) iridium, a green light emitting molecule, and has the following structure:
the iridium heterocomplex taking 2-phenylpyridine and 2- (4-dibenzofuran) -pyridine as ligands is a widely applied organic phosphorescent material. The dibenzofuran structure expands the conjugated plane of the ligand, reduces the LUMO orbital level of the complex, leads to red shift of the luminescence of the material, and reduces the unsaturated green light component. As shown in Table 1, the maximum absorption wavelength of complex 1 was 516nm, and the maximum absorption wavelength of complex 2 was 528 nm. When the substituted segment of aza-dibenzofuran is introduced, the electron withdrawing property of the group is enhanced, and the LUMO energy level of the complex is reduced. The pyridofurobenzenes complex 3 was blue-shifted by 5nm compared to the dibenzofuran complex 2. This makes complex 3 more suitable for application as a saturated green color in a display.
TABLE 1 Structure, Redox potential and absorption maximum wavelength of the different complexes
The patent reports that a four-coordinate platinum complex (US 20160285014A1) and a six-coordinate iridium complex (EP 2982729A1) have the following structures as an emitter of an OLED phosphorescent material:
the complexes contain small molecules of 2-methyl-8- (2-pyridyl) benzofuran [2,3-b ] pyridine, and the industrial preparation of the compounds has wide market prospect.
The synthesis method of 2-methyl-8- (2-pyridyl) benzofuran [2,3-b ] pyridine was reported for the first time in 2006 (patent number: EP 2730583A 1), and the synthesis method is shown as the following formula:
the starting material is 2-amino-3-bromo-6-methylpyridine, which is coupled with 2, 3-dimethoxyphenylboronic acid to obtain 3- (2, 3-dimethoxyphenyl) -6-methyl-2-aminopyridine, and the 8-methoxy-2-methylbenzofuran [2,3-b ] pyridine is generated by ring closure under the action of tert-butyl nitrite. The pyridine hydrochloride and the product are heated together, methyl is removed to generate 8-hydroxy-2-methylbenzofuran [2,3-b ] pyridine, the pyridine hydrochloride and trifluoromethanesulfonic anhydride are subjected to esterification reaction to generate 8-trifluoromethanesulfonate-2-methylbenzofuran [2,3-b ] pyridine, and finally the pyridine hydrochloride and 2-pyridyl zinc bromide are coupled to obtain a final product, namely 2-methyl-8- (2-pyridyl) benzofuran [2,3-b ] pyridine. The price of the starting material 2-amino-3-bromo-6-methylpyridine is very high, 2, 3-dimethoxyphenylboronic acid also needs to be prepared from o-dimethoxybenzene, and the cost of the raw materials in the route is too high. In addition, the first step of the suzuki coupling reaction needs to use 3% of tetratriphenylphosphine palladium, and the tetratriphenylphosphine palladium has high activity and is easy to oxidize and deteriorate, so that a large amount of noble metal catalyst is needed to be consumed. The coupling reaction has higher operation requirement, needs inert gas protection, generates a large amount of waste water containing organic solvent and salt, and improves the cost of dangerous waste treatment.
In view of the wide market prospect of 2-methyl-8- (2-pyridyl) benzofuran [2,3-b ] pyridine, people are prompted to research a process route with lower cost, simpler operation and less generation of chemical waste. Wherein, the 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine is a key intermediate for producing the 2-methyl-8- (2-pyridyl) benzofuran [2,3-b ] pyridine, a more efficient, economic and green production process of the 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine is sought, and the method has good economic and social benefits.
Disclosure of Invention
In order to solve the problems, the invention provides a synthetic method of 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine, which has the advantages of high yield, low production cost, simple post-treatment, less chemical waste and suitability for process amplification; in addition, the method does not need to adopt expensive 2-amino-3-bromo-6-methylpyridine and noble metal catalysts, the raw materials are cheap and commercially available, inert atmosphere protection is not needed, and the method is simple in subsequent treatment and environment-friendly.
The object of the invention is achieved in the following way:
a synthetic method of 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine comprises the following reaction steps:
a synthetic method of 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine is realized by the following steps:
a) adding 2-chloro-3-nitro-6-methylpyridine, guaiacol and DABCO into a reaction kettle, heating to 125 ℃ and 135 ℃, stirring for reaction for 3-4h, then stopping heating, adding 1, 2-dichloroethane to continue stirring and returning to room temperature when the temperature of a reaction mixed solution is reduced to 78-82 ℃, adding water into the mixed solution in the reaction kettle for washing and separating, spin-drying an organic phase and recovering an organic solvent, pulping and dispersing a concentrated phase by using petroleum ether, and performing suction filtration and drying to obtain 2- (2-methoxyphenoxy) -6-methyl-3-nitropyridine;
b) dissolving the obtained 2- (2-methoxyphenoxy) -6-methyl-3-nitropyridine in ethanol, adding palladium carbon, heating to 70-75 ℃, dropwise adding hydrazine hydrate, reacting for 2-3h, filtering the mixture, recovering palladium carbon, spin-drying the solvent (ethanol), pulping a concentrated phase by using petroleum ether, and drying a filter cake after suction filtration to obtain 2- (2-methoxyphenoxy) -6-methyl-3-aminopyridine;
c) mixing the obtained 2- (2-methoxyphenoxy) -6-methyl-3-aminopyridine with cuprous iodide and dimethyl sulfoxide, heating to 78-82 ℃, dropwise adding isoamyl nitrite, reacting for 30-40min, then adding water and a petroleum ether solution containing ethyl acetate for extraction, washing an organic phase with water, decoloring by using a silica gel column, and spin-drying a permeate liquid to obtain the product 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine.
The molar ratio of 2-chloro-3-nitro-6-methylpyridine, guaiacol and DABCO in step a) is 1:1-1.5: 1-1.5.
In the step b), the palladium carbon is wet palladium carbon with the palladium content of 10%, and the using amount of the wet palladium carbon is 4-10% of the mass of the 2- (2-methoxyphenoxy) -6-methyl-3-nitropyridine.
The mol ratio of the 2- (2-methoxyphenoxy) -6-methyl-3-nitropyridine to the hydrazine hydrate in the step b) is 1: 2-3.
The dosage of the cuprous iodide in the step c) is 4-10% of the mass of the 2- (2-methoxyphenoxy) -6-methyl-3-aminopyridine.
The dosage of the isoamyl nitrite in the step c) is 1 to 1.5 of the molar weight of the 2- (2-methoxyphenoxy) -6-methyl-3-aminopyridine.
In the petroleum ether solution containing ethyl acetate in the step c), the molar ratio of ethyl acetate to petroleum ether is 1: 2-6.
The rotary evaporator used for the spin-drying has the temperature of 35-60 ℃ and the rotating speed of 30-40 rpm.
The synthesis method disclosed by the invention is characterized in that a carbon-oxygen bond is constructed through nucleophilic substitution reaction of 2-chloro-3-nitro-6-methylpyridine and guaiacol under an alkaline condition, and then hydrazine hydrate is used for reducing nitro to generate corresponding arylamine under the catalysis of palladium-carbon. The arylamine is subjected to ring closure under the action of isoamyl nitrite to synthesize the 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine.
Compared with the prior art, the invention has the beneficial effects that: 1. the reaction avoids the use of expensive 2-amino-3-bromo-6-methylpyridine; 2. the reaction adopts nucleophilic substitution reaction with simple operation to carry out fragment docking, thereby avoiding the use of noble metal catalyst sensitive to air and the Suzuki coupling reaction with higher operation requirement; 3. the reaction avoids the generation of wastewater containing salt and organic solvent, and the solvent can be recycled, thus meeting the requirement of green chemistry; 4. all raw materials are low in price and commercially available, expensive 2, 3-dimethoxy phenylboronic acid is not needed, 5 and Pd/C obtained by catalytic reduction can be recycled, and the cost of the raw materials is further reduced.
Drawings
FIG. 1 is a schematic representation of 2- (2-methoxyphenoxy) -6-methyl-3-nitropyridine prepared in example 11H-NMR spectrum.
FIG. 2 is a schematic representation of 2- (2-methoxyphenoxy) -6-methyl-3-nitropyridine prepared in example 113C-NMR spectrum.
FIG. 3 is a photograph of 2- (2-methoxyphenoxy) -6-methyl-3-aminopyridine prepared in example 11H-NMR spectrum.
FIG. 4 is a photograph of 2- (2-methoxyphenoxy) -6-methyl-3-aminopyridine prepared in example 113C-NMR spectrum.
FIG. 5 is 2-methyl-8-methoxybenzofuran [2,3-b ] prepared in example 1]Process for preparing pyridine1H-NMR spectrum.
FIG. 6 is 2-methyl-8-methoxybenzofuran [2,3-b ] prepared in example 1]Process for preparing pyridine13C-NMR spectrum.
Detailed Description
Example 1:
(1) synthesis of 2- (2-methoxyphenoxy) -6-methyl-3-nitropyridine
In a 50L glass reaction kettle provided with a reflux condenser tube and mechanical stirring,adding 3Kg of 2-chloro-3-nitro-6-methylpyridine, 2.30Kg of guaiacol and 2.34Kg of DABCO, setting the heating temperature of an oil bath at 130 ℃ for reaction for 3-4h, and stopping heating when the peak of the raw material 2-chloro-3-nitro-6-methylpyridine is completely disappeared by the detection of a liquid chromatogram detection means during sampling; when the temperature of the oil bath is reduced to 80 ℃, adding 30L of 1, 2-dichloroethane, stirring and dispersing, continuously cooling to room temperature, then filtering, soaking the filter cake with 5L of 1, 2-dichloroethane, pumping green, adding water into the obtained filter cake, stirring and washing for 15 minutes, stopping stirring, and separating liquid; decolorizing the organic phase with silica gel column, spin drying to recover 1, 2-dichloroethane to obtain yellow oily matter, adding 10L petroleum ether into the yellow oily matter, pulping, dispersing, vacuum filtering, and drying to obtain light yellow solid 4.01Kg1H-NMR and13the structure was determined to be 2- (2-methoxyphenoxy) -6-methyl-3-nitropyridine by C-NMR, and the purity was 98% and the yield was 89% by liquid chromatography.
(2) Synthesis of 2- (2-methoxyphenoxy) -6-methyl-3-aminopyridine
Adding 3Kg of 2- (2-methoxyphenoxy) -6-methyl-3-nitropyridine prepared in the step (1), 150g of wet palladium carbon containing 10% of palladium and 30L of absolute ethanol into a 50L glass reaction kettle provided with a reflux condenser pipe and mechanical stirring, and heating to 70 ℃ under stirring; dropwise adding 1.5L of hydrazine hydrate into a dropping funnel, reacting for 2 hours, stopping heating, returning the temperature to room temperature, filtering and recovering palladium carbon, spin-drying ethanol in a mixed solution to obtain a light yellow oily substance, adding 12L of petroleum ether into the light yellow oily substance, pulping, dispersing, suction filtering, and vacuum drying to obtain 2.24Kg of white-like solid, wherein the white-like solid is obtained by1H-NMR and13the structure was confirmed to be 2- (2-methoxyphenoxy) -6-methyl-3-aminopyridine by C-NMR, the purity by liquid chromatography was 98%, and the yield was 84%.
(3) Synthesis of 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine
Adding 1.5Kg of 2- (2-methoxyphenoxy) -6-methyl-3-aminopyridine prepared in the step (2), 75g of cuprous iodide and 30L of dimethyl sulfoxide into a 50L double-layer low-temperature kettle, heating to 80 ℃ in an oil bath, slowly dropwise adding 920g of isoamyl nitrite, and after the addition is finishedKeeping the temperature to 80 ℃ for reaction, sampling, adopting a liquid chromatography detection means to detect that the peak of the raw material 2- (2-methoxyphenoxy) -6-methyl-3-aminopyridine is completely disappeared, adding the reaction solution into 60L of water, then adding 25L of petroleum ether and 5L of ethyl acetate, fully stirring, separating out a water phase, washing an organic phase with water, then washing with a saturated sodium chloride solution, then decoloring with a silica gel column, spin-drying the permeation solution to obtain 0.95Kg of white solid, and carrying out liquid chromatography detection on the obtained white solid to obtain 0.95Kg of white solid1H-NMR and13C-NMR confirmed 2-methyl-8-methoxybenzofuran [2,3-b ] structure]Pyridine, yield 63%, product purity 99% by liquid chromatography.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various changes and modifications can be made without departing from the overall concept of the present invention, and these should also be considered as the protection scope of the present invention.
Claims (7)
1. A synthetic method of 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine is characterized by comprising the following reaction steps:
a) adding 2-chloro-3-nitro-6-methylpyridine, guaiacol and DABCO into a reaction kettle, heating to 125-phase 135 ℃, stirring for reaction for 3-4h, sampling, detecting that the peak of the raw material 2-chloro-3-nitro-6-methylpyridine completely disappears by using a liquid chromatography detection means, stopping heating, adding 1, 2-dichloroethane for continuously stirring to room temperature when the temperature of a reaction mixed solution is reduced to 78-82 ℃, then adding water into the mixed solution in the reaction kettle for washing and separating liquid, spin-drying the organic phase and recovering an organic solvent, pulping and dispersing a concentrated phase by using petroleum ether, and performing suction filtration and drying to obtain 2- (2-methoxyphenoxy) -6-methyl-3-nitropyridine;
b) dissolving the obtained 2- (2-methoxyphenoxy) -6-methyl-3-nitropyridine in ethanol, adding palladium carbon, heating to 70-75 ℃, dropwise adding hydrazine hydrate, reacting for 2-3h, filtering the mixture, recovering palladium carbon, spin-drying the solvent, pulping a concentrated phase by using petroleum ether, and drying a filter cake after suction filtration to obtain 2- (2-methoxyphenoxy) -6-methyl-3-aminopyridine;
c) mixing the obtained 2- (2-methoxyphenoxy) -6-methyl-3-aminopyridine with cuprous iodide and dimethyl sulfoxide, heating to 78-82 ℃, dropwise adding isoamyl nitrite, reacting for 30-40min, then adding water and a petroleum ether solution containing ethyl acetate for extraction, washing an organic phase with water, decoloring by using a silica gel column, and spin-drying a permeate liquid to obtain a product 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine;
the dosage of the cuprous iodide in the step c) is 4-10% of the mass of the 2- (2-methoxyphenoxy) -6-methyl-3-aminopyridine.
2. The method for synthesizing 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine according to claim 1, wherein the molar ratio of 2-chloro-3-nitro-6-methylpyridine, guaiacol and DABCO in step a) is 1:1-1.5: 1-1.5.
3. The method for synthesizing 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine according to claim 1, wherein the palladium carbon in the step b) is wet palladium carbon with a palladium content of 10%, and the amount of the wet palladium carbon is 4-10% of the mass of 2- (2-methoxyphenoxy) -6-methyl-3-nitropyridine.
4. The method for synthesizing 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine according to claim 1, wherein the molar ratio of 2- (2-methoxyphenoxy) -6-methyl-3-nitropyridine to hydrazine hydrate in step b) is 1: 2-3.
5. The method for synthesizing 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine according to claim 1, wherein the amount of isoamyl nitrite used in step c) is 1 to 1.5 times of the molar amount of 2- (2-methoxyphenoxy) -6-methyl-3-aminopyridine.
6. The method for synthesizing 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine according to claim 1, wherein the molar ratio of ethyl acetate to petroleum ether in the petroleum ether solution containing ethyl acetate in the step c) is 1: 2-6.
7. The method for synthesizing 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine according to claim 1, wherein the rotary evaporator used for the spin drying is 35-60 ℃ and the rotation speed is 30-40 rpm.
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| CN101037405A (en) * | 2007-04-20 | 2007-09-19 | 大连理工大学 | Preparation method of aniline derivative containing 2-hydroxyethylsulfonyl |
| WO2011132051A2 (en) * | 2010-04-19 | 2011-10-27 | Glenmark Pharmaceuticals S.A. | Tricycle compounds as phosphodiesterase-10 inhibitors |
| CN107445886A (en) * | 2017-05-24 | 2017-12-08 | 北京八亿时空液晶科技股份有限公司 | A kind of preparation method of the phenyl carbazole of 3 bromine of high-purity 9 |
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