CN110105337A - A kind of quinolines triarylamine and preparation method thereof - Google Patents

A kind of quinolines triarylamine and preparation method thereof Download PDF

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CN110105337A
CN110105337A CN201910465999.XA CN201910465999A CN110105337A CN 110105337 A CN110105337 A CN 110105337A CN 201910465999 A CN201910465999 A CN 201910465999A CN 110105337 A CN110105337 A CN 110105337A
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CN110105337B (en
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邱仁华
严明盼
朱龙志
神户宣明
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Hunan University
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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

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Abstract

The present invention is a kind of method for preparing quinolines triarylamine and preparation method thereof.With substituted 8- amido quinolines (I) and carbazole compound (II) for substrate, it is 1% to 30% (relative to level-one amine compounds I that molar fraction, which is added, Raney nickel similarly hereinafter), the alkali of 2-5 molar equivalent, 2mL organic solvent is solvent, under nitrogen atmosphere, reaction mixture is stirred to react 1-48 hours at 25 DEG C to 160 DEG C, saturated ammonium chloride solution is added after fully reacting to be quenched, it is extracted with polar organic solvent, anhydrous sodium sulfate is added or anhydrous magnesium sulfate is dry, it is concentrated through Rotary Evaporators, pillar layer separation obtains target product triarylamine compound (III).The advantages that this method has cheap catalyst, and yield is high, easy to operate, and no harmful side product generates, for realizing that its industrialized production has certain feasibility.Obtained quinolines triaryl aminated compounds is synthesized, various functional moleculars can be converted by various tandem reactions or cross-coupling reaction, have potential application value to biological medicine, Material Field.

Description

A kind of quinolines triarylamine and preparation method thereof
[technical field]
The invention belongs to be catalyzed organic synthesis field, a kind of 8- amido quinolines to replace are related in particular to The new of quinolyl triaryl aminated compounds is prepared in the case where transiting metal nickel is as catalysts conditions with substituted carbazole class compound Method.This method is main with the carbazole compound of 8- amido quinolines, different substituents containing different substituents Raw material, makees catalyst with transiting metal nickel, polar organic solvent is that solvent, inorganic salts make alkali, in N2Under atmosphere 25-160 DEG C it is anti- 1-48h is answered, higher yields prepare quinolyl triaryl aminated compounds.
[background technique]
Triaryl aminated compounds is a kind of important compound, the triarylamine of especially big steric hindrance and big conjugated system Compound has a wide range of applications in fields in photoelectric material, medicine intermediate, organic dyestuff etc..In recent years, organic functions material Expect the more and more important role of performer in daily production and life.With the rapid development of Organic Light Emitting Diode, especially Display technology have many advantages, such as self-luminous, wide viewing angle, almost infinite high contrast, compared with low power consumption, high reaction speed, and The material of OLED hole-transporting layer is mainly triarylamine.How this is but also to efficiently synthesize triaryl amine as vast organic conjunction The research direction of Cheng research worker.Tri-arylamine group compound plays the role of particularly important, but its synthesis is not easy to.It passes The method of the synthesis triarylamine of system mainly from diaryl amine, by Buchwald-Hartwig coupling reaction or Further arylation is realized in Ullmann condensation reaction.In traditional synthetic method, the synthesis of triaryl amine is realized.In recent years, By realizing that building triarylamine also makes some progress from primary amine directness.2009, YasuhiroUozumi et al., which is reported, is supported on palladium on amphipathic PS-PEG resin, realizes catalysis triaryl amine reaction； 2015, Mikhail S.Nechaev et al., which is reported, constructed triaryl amine by a kind of expansion loop N- heterocycle carbine palladium complex Method.And the reaction of the building triarylamine for cheap metal catalysis, 2002, RaghunathV.Chaudhari et al. Report the synthesis slave primary amine to triarylamine of copper catalysis.However for the aromatic hydrocarbons of big steric hindrance, since big steric effect is not easy Make reaction efficiency low in the oxidation addition of metallic catalyst.Based on above-mentioned report, we devise a kind of cheap transition gold Belong to nickel catalyst system.Choosing, there is the 8- aminoquinoline of coordination ability to make reaction substrate, form efficient cooperation with catalyst nickel Object, the activation energy after reducing diaryl amine and metal coordination, promotes diaryl-amine to triaryl amine transformation efficiency, to realize by primary Amine sets out the big steric hindrance tri-arylamine group compound of one pot process.Cheap metal nickel is catalyzed primary amine and big steric hindrance bromo carbazole derivative One kettle way forms the realization of triarylamine, has certain prospects for commercial application.
[summary of the invention]
It is an object of that present invention to provide the new methods that one kind prepares quinolyl triaryl aminated compounds (III).Its preparation side Method be using the carbazole compound II of 8- amido quinolines I, different substituents containing different substituents as primary raw material, Use transiting metal nickel as catalyst, using polar organic solvent as solvent, inorganic salts make alkali, in N225-160 DEG C of reaction under atmosphere 1-48h, higher yields prepare quinolyl triaryl aminated compounds.This method has yield height, easy to operate, realizes its industry Metaplasia, which produces, has certain feasibility.
It is characterized in that, the substrate primary amine I is 8- aminoquinoline (R1=hydrogen), 8- amino -5- phenylsulfanylquinoline (R1= 5- sulfur phenenyl), 8- amino -6- methoxy quinoline (R1=6- methoxyl group), 8- amino-5-phenyl quinoline (R1=5- phenyl), 8- ammonia Base -2- methylquinoline (R1=2- methyl), 8- amino-4-phenyl quinoline (R1=4- phenyl), 8- amino -5,7- dichloroquinoline (R1 One of=5,7- dichloro)；
Substrate carbazole II is 9- (4- bromophenyl) carbazole (R2=hydrogen), 9- (4- bromophenyl) -3,6- di-t-butyl carbazole (R2 =3,6- di-t-butyl), 9- (4- bromophenyl) -3,6- dibromo carbazole (R2=3,6- dibromo), 9- (4- bromophenyl) -2,7- dibromo Carbazole (R2=2,7- dibromo), 9- (4- bromophenyl) -1,8- diphenyl sulfide carbazole (R2=1,8- hexichol sulfenyl), 9- (4- bromobenzene Base) -1,8- diphenyl carbazole (R2=1,8- diphenyl), 9- (4- bromophenyl) -1- phenyl carbazole (R2=1- phenyl), 9- (4- bromine Phenyl) -1- diphenyl sulfide carbazole (R2=1- thiophenyl), one kind of 9- (4- bromophenyl) -1.2.3.4- tetrahydro carbazole, dosage is 2.0 equivalents to 5.0 equivalents；
Substrate III is quinolyl triarylamine, the phenyl ring contraposition of the nitrogen-atoms of quinoline amino and two molecule carbazole derivates It is connected.
To achieve the above object of the invention, the present invention proposes technical solution below:
Synthetic route is shown in Figure of description, it is characterised in that: with substituted 8- amido quinolines I and bromo carbazole Class compound II is substrate, and Raney nickel, 1- that molar fraction was 1% to 30% (relative to primary amino-compound I, similarly hereinafter) is added The alkali of 5 molar equivalents, common organic solvents are solvent, and under nitrogen atmosphere, reaction mixture is stirred to react 1- at 25 DEG C to 160 DEG C 48 hours, after fully reacting be added saturated ammonium chloride solution be quenched, extracted with polar organic solvent, be added anhydrous sodium sulfate or Anhydrous magnesium sulfate is dry, obtains target product triarylamine compound III through Rotary Evaporators concentration, pillar layer separation.
In above-mentioned preparation method, the reaction dissolvent is tetrahydrofuran, dimethyl sulfoxide, N-Methyl pyrrolidone, N, N- One kind of dimethylformamide, DMAC N,N' dimethyl acetamide, toluene, paraxylene, acetonitrile.
In above-mentioned preparation method, Raney nickel used is nickel fluoride, nickel chloride, nickelous bromide, nickel acetate, nickel sulfate, acetic acid Nickel, trifluoroacetic acid nickel, trifluoromethanesulfonic acid nickel, nickel acetylacetonate, (bis- (diphenylphosphine) ferrocene of 1,1'-) Nickel Chloride, it is double- (1,5- cyclo-octadiene) nickel (Ni (COD)2), dosage is 1% to 30% mole.
In above-mentioned preparation method, the alkali is potassium carbonate, sodium carbonate, saleratus, sodium bicarbonate, cesium carbonate, the tert-butyl alcohol One kind of sodium, potassium tert-butoxide, dosage are 2-5 equivalent.
In above-mentioned preparation method, the reaction condition be 25-160 DEG C reaction 1-48 hours.
Method provided by the invention is to prepare quinolyl triaryl aminated compounds to develop an efficient new way.Its Advantage is that yield is high, easy to operate from primary amine one pot process using cheap metal catalyst.
[Detailed description of the invention]
It is the synthesis path figure of quinolyl triaryl aminated compounds (III) provided by the invention shown in attached drawing.
[specific embodiment]
It is provided by the present invention with substituted 8- amido quinolines and substituted carbazole class compound in transiting metal nickel As the method for preparing quinolyl triaryl aminated compounds under catalysts conditions.This method is with the 8- amido containing different substituents Quinolines I, different substituents carbazole compound II be primary raw material, use transiting metal nickel as catalyst, with Polar organic solvent is solvent, and inorganic salts make alkali, in N225-160 DEG C of reaction 1-48h, higher yields prepare quinolyl under atmosphere Triaryl aminated compounds.
Below with reference to specific preparating example, the present invention will be further described:
Preparation example 1
Magnetic stir bar 1,8- amino -5- sulfur phenenyl quinoline (0.3mmol), 9- (4- bromine are added in 10mL reaction tube Phenyl) carbazole (0.6mmol), nickel chloride (0.06mmol), potassium carbonate (1.2mmol), it vacuumizes and fills out nitrogen 3 times, nitrogen atmosphere Lower addition tetrahydrofuran (2mL) is reacted 24 hours in the environment of 100 DEG C.After reaction, saturated aqueous ammonium chloride is added It is quenched, after ethyl acetate extraction, dry, concentration, obtains N, N- bis- (4- (9H- carbazole -9- base) phenyl) -5- through pillar layer separation (thiophenyl) -8- amido quinoline, yield 97%.
Preparation example 2
Magnetic stir bar 1,8- aminoquinoline (0.3mmol), 9- (4- bromophenyl) carbazole are added in 10mL reaction tube (0.6mmol), nickelous bromide (0.06mmol), potassium carbonate (1.2mmol) vacuumize and fill out nitrogen 3 times, tetrahydro is added under nitrogen atmosphere Furans (2mL) reacts 24 hours in the environment of 100 DEG C.After reaction, saturated aqueous ammonium chloride is added to be quenched, acetic acid After ethyl ester extraction, dry, concentration, N is obtained through pillar layer separation, N- bis- (4- (9H- carbazole -9- base) phenyl) -8- amido quinoline produces Rate is 95%.
Preparation example 3
Magnetic stir bar 1,8- amino -6- methoxy quinoline (0.3mmol), 9- (4- bromine are added in 10mL reaction tube Phenyl) carbazole (0.6mmol), nickel fluoride (0.03mmol), potassium carbonate (0.9mmol), it vacuumizes and fills out nitrogen 3 times, nitrogen atmosphere Lower addition tetrahydrofuran (2mL) is reacted 24 hours in the environment of 100 DEG C.After reaction, saturated aqueous ammonium chloride is added It is quenched, after ethyl acetate extraction extraction, dry, concentration, obtains N, N- bis- (4- (9H- carbazole -9- base) phenyl)-through pillar layer separation 6- (methoxyl group) -8- amido quinoline, yield 93%.
Preparation example 4
Magnetic stir bar 1,8- amino-5-phenyl quinoline (0.3mmol), 9- (4- bromobenzene are added in 10mL reaction tube Base) carbazole (0.6mmol), nickel fluoride (0.03mmol), potassium carbonate (0.9mmol), it vacuumizes and fills out nitrogen 3 times, under nitrogen atmosphere It is added tetrahydrofuran (2mL), is reacted 24 hours in the environment of 100 DEG C.After reaction, saturated aqueous ammonium chloride is added to quench It goes out, after ethyl acetate extraction extraction, dry, concentration, obtains N, N- bis- (4- (9H- carbazole -9- base) phenyl) -5- through pillar layer separation (phenyl) -8- amido quinoline, yield 91%.
Preparation example 5
Magnetic stir bar 1,8- amino-2-methyl quinoline (0.3mmol), 9- (4- bromobenzene are added in 10mL reaction tube Base) carbazole (0.6mmol), nickel acetylacetonate (0.03mmol), potassium carbonate (0.9mmol), it vacuumizes and fills out nitrogen 3 times, nitrogen atmosphere Lower addition tetrahydrofuran (2mL) is enclosed, is reacted 24 hours in the environment of 100 DEG C.After reaction, it is water-soluble that saturated ammonium chloride is added Liquid is quenched, and after ethyl acetate extraction extraction, dry, concentration, obtains N, (4- (9H- carbazole -9- base) benzene of N- bis- through pillar layer separation Base) -2- (methyl) -8- amido quinoline, yield 90%.
Preparation example 6
Magnetic stir bar 1, the bromo- 8- aminoquinoline of 5-, 9- (4- bromophenyl) carbazole are added in 10mL reaction tube (0.6mmol), nickel sulfate (0.03mmol), potassium carbonate (0.9mmol) vacuumize and fill out nitrogen 3 times, diformazan is added under nitrogen atmosphere Base sulfoxide (2mL) reacts 24 hours in the environment of 100 DEG C.After reaction, saturated aqueous ammonium chloride is added to be quenched, second After acetoacetic ester extraction extraction, dry, concentration, N, N- bis- (4- (9H- carbazole -9- base) phenyl) bromo- 8- of -5- are obtained through pillar layer separation Amido quinoline, yield 89%.
Preparation example 7
Magnetic stir bar 1,8- aminoquinoline (0.3mmol), 9- (4- bromophenyl) carbazole are added in 10mL reaction tube (0.6mmol), nickel chloride (0.06mmol), potassium tert-butoxide (1.2mmol) vacuumize and fill out nitrogen 3 times, be added four under nitrogen atmosphere Hydrogen furans (2mL) reacts 1 hour in the environment of 160 DEG C.After reaction, saturated aqueous ammonium chloride is added to be quenched, acetic acid After ethyl ester extraction, dry, concentration, N, N- bis- (4- (9H- carbazole -9- base)) -8- amido quinoline are obtained through pillar layer separation, yield is 95%.The excitation wavelength of gained compound is 260-400nm, launch wavelength 540nm, has biggish stoke shift.
Preparation example 8
In 10mL reaction tube be added magnetic stir bar 1,8- aminoquinoline, 9- (4- bromophenyl) carbazole (0.6mmol), Nickel sulfate (0.03mmol), potassium carbonate (0.6mmol) are vacuumized and are filled out nitrogen 3 times, and tetrahydrofuran (2mL) is added under nitrogen atmosphere, It is reacted 48 hours in the environment of 25 DEG C.After reaction, saturated aqueous ammonium chloride is added to be quenched, ethyl acetate extraction extraction After taking, dry, being concentrated, N, N- bis- (4- (9H- carbazole -9- base)) -8- amido quinoline, yield 70% are obtained through pillar layer separation.
Preparation example 10
Magnetic stir bar 1,8- aminoquinoline (0.3mmol), 9- (4- bromophenyl) carbazole are added in 10mL reaction tube (0.6mmol), trifluoroacetic acid nickel (0.003mmol), potassium carbonate (1.5mmol) are vacuumized and are filled out nitrogen 3 times, are added under nitrogen atmosphere Enter N-Methyl pyrrolidone (2mL), is reacted 24 hours in the environment of 100 DEG C.After reaction, it is water-soluble that saturated ammonium chloride is added Liquid is quenched, and after ethyl acetate extraction extraction, dry, concentration, obtains N, (4- (9H- carbazole -9- the base)-benzene of N- bis- through pillar layer separation Base) -8- amido quinoline, yield 75%.
Preparation example 11
Magnetic stir bar 1,8- aminoquinoline (0.3mmol), 9- (4- bromophenyl) -3,6- are added in 10mL reaction tube Di-t-butyl carbazole (0.6mmol), trifluoroacetic acid nickel (0.09mmol), potassium carbonate (0.9mmol), vacuumize and fill out nitrogen 3 times, nitrogen Atmosphere encloses lower addition tetrahydrofuran (2mL), reacts 24 hours in the environment of 100 DEG C.After reaction, saturated ammonium chloride is added Aqueous solution is quenched, and after ethyl acetate extraction extraction, dry, concentration, obtains N, (4- (the tertiary fourth of 9H-3,6- bis- of N- bis- through pillar layer separation Base carbazole -9- base)-phenyl) -8- amido quinoline, yield 87%.
Preparation example 12
Magnetic stir bar 1,8- aminoquinoline (0.3mmol), 9- (4- bromophenyl) -3,6- are added in 10mL reaction tube Di-t-butyl carbazole (0.6mmol), trifluoromethanesulfonic acid nickel (0.03mmol), potassium carbonate (0.9mmol) are vacuumized and are filled out nitrogen 3 times, N,N-dimethylacetamide (2mL) is added under nitrogen atmosphere, is reacted 24 hours in the environment of 100 DEG C.After reaction, it is added Saturated aqueous ammonium chloride is quenched, and after ethyl acetate extraction extraction, dry, concentration, obtains N, the (4- (9H- of N- bis- through pillar layer separation 3,6- di-t-butyl carbazole -9- bases)-phenyl) -8- amido quinoline, yield 88%.
Preparation example 13
1 son of magnetic agitation, 8- aminoquinoline (0.3mmol), 9- (4- bromophenyl) -3,6- are added in 10mL reaction tube Dibromo carbazole (0.6mmol), nickel acetylacetonate (0.03mmol), sodium carbonate (0.9mmol), vacuumize and fill out nitrogen 3 times, nitrogen atmosphere Lower addition toluene (2mL) is enclosed, is reacted 24 hours in the environment of 100 DEG C.After reaction, saturated aqueous ammonium chloride is added to quench It goes out, after ethyl acetate extraction extraction, dry, concentration, obtains N, (4- (9H-3,6- dibromo the carbazole -9- of N- bis- through pillar layer separation Base)-phenyl) -8- amido quinoline, yield 89%.
Preparation example 14
1 son of magnetic agitation, 8- aminoquinoline (0.3mmol), 9- (4- bromophenyl)-are added in 10mL reaction tube 1.2.3.4- tetrahydro carbazole (0.6mmol), (bis- (diphenylphosphine) ferrocene of 1,1'-) Nickel Chloride (0.03mmol), bicarbonate Sodium (0.9mmol) is vacuumized and is filled out nitrogen 3 times, n,N-dimethylacetamide (2mL) is added under nitrogen atmosphere, in 100 DEG C of environment Lower reaction 24 hours.After reaction, saturated aqueous ammonium chloride is added to be quenched, ethyl acetate extraction extraction, dry, concentration Afterwards, N, N- bis- (4- (9H-1.2.3.4- tetrahydro carbazole -9- base)-phenyl) -8- amido quinoline are obtained through pillar layer separation, yield is 90%.
Preparation example 15
Magnetic stir bar 1, the bromo- 8- aminoquinoline of 4- phenyl -5-, 9- (4- bromophenyl) click are added in 10mL reaction tube Azoles (0.6mmol), double-(1,5- cyclo-octadiene) nickel (Ni (COD)2) (0.03mmol), saleratus (0.9mmol), it vacuumizes It fills out nitrogen 3 times, paraxylene (2mL) is added under nitrogen atmosphere, is reacted 24 hours in the environment of 100 DEG C.After reaction, add Enter saturated aqueous ammonium chloride to be quenched, after ethyl acetate extraction extraction, dry, concentration, obtains N, bis- (4- of N- through pillar layer separation (9H- carbazole -9- base) phenyl) the bromo- 8- amido quinoline of -4- phenyl -5-, yield 85%.
Preparation example 16
Magnetic stir bar 1, the bromo- 8- aminoquinoline of 4- phenyl -5-, 9- (4- bromophenyl) click are added in 10mL reaction tube Azoles (0.6mmol), nickel sulfate (0.03mmol), cesium carbonate (0.9mmol) vacuumize and fill out nitrogen 3 times, second is added under nitrogen atmosphere Nitrile (2mL) reacts 24 hours in the environment of 100 DEG C.After reaction, saturated aqueous ammonium chloride is added to be quenched, acetic acid second After ester extraction extraction, dry, concentration, N, N- bis- (4- (9H- carbazole -9- base) phenyl) -4- phenyl -8- amine are obtained through pillar layer separation Base quinoline, yield 86%.
Preparation example 17
Magnetic stir bar 1,8- aminoquinoline, 9- (4- bromophenyl) carbazole (0.6mmol) are added in 10mL reaction tube, Nickel sulfate (0.03mmol), sodium tert-butoxide (0.9mmol) vacuumize and fill out nitrogen 3 times, tetrahydrofuran is added under nitrogen atmosphere (2mL) reacts 24 hours in the environment of 100 DEG C.After reaction, saturated aqueous ammonium chloride is added to be quenched, ethyl acetate After extraction extraction, dry, concentration, N, N- bis- (4- (9H-3- bromine carbazole -9- base) phenyl) -4- phenyl -8- are obtained through pillar layer separation Amido quinoline, yield 86%.
Preparation example 18
1 son of magnetic agitation, the chloro- 8- aminoquinoline (0.3mmol) of 5-, 9- (4- bromobenzene are added in 10mL reaction tube Base) -1.2.3.4- tetrahydro carbazole (0.6mmol), trifluoroacetic acid nickel (0.03mmol), potassium tert-butoxide (0.9mmol) are vacuumized and are filled out Nitrogen 3 times, tetrahydrofuran (2mL) is added under nitrogen atmosphere, is reacted 24 hours in the environment of 100 DEG C.After reaction, it is added Saturated aqueous ammonium chloride is quenched, and after ethyl acetate extraction extraction, dry, concentration, obtains N, the (4- (9H- of N- bis- through pillar layer separation 1.2.3.4- tetrahydro carbazole -9- base)-phenyl) the chloro- 8- amido quinoline of -5-, yield 90%.
The embodiments described above only express several embodiments of the present invention, and the description thereof is more specific and detailed, but simultaneously Limitations on the scope of the patent of the present invention therefore cannot be interpreted as.It should be pointed out that for those of ordinary skill in the art For, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to guarantor of the invention Protect range.Therefore, the scope of protection of the patent of the invention shall be subject to the appended claims.

Claims (5)

1. a kind of preparation method of quinolyl triarylamine, the raw material (aminoquinoline I and bromo-derivative II) and target compound The structural formula of triarylamine III is as follows:
It is characterized in that, the substrate primary amine I is 8- aminoquinoline (R1=hydrogen), 8- amino -5- phenylsulfanylquinoline (R1=5- sulphur Phenyl), 8- amino -6- methoxy quinoline (R1=6- methoxyl group), 8- amino-5-phenyl quinoline (R1=5- phenyl), 8- amino- 2- methylquinoline (R1=2- methyl), 8- amino-4-phenyl quinoline (R1=4- phenyl), 8- amino -5,7- dichloroquinoline (R1= One of 5,7- dichloro)；
Substrate carbazole II is 9- (4- bromophenyl) carbazole (R2=hydrogen), 9- (4- bromophenyl) -3,6- di-t-butyl carbazole (R2=3, 6- di-t-butyl), 9- (4- bromophenyl) -3,6- dibromo carbazole (R2=3,6- dibromo), 9- (4- bromophenyl) -2,7- dibromo carbazole (R2=2,7- dibromo), 9- (4- bromophenyl) -1,8- diphenyl sulfide carbazole (R2=1,8- hexichol sulfenyl), 9- (4- bromophenyl) -1, 8- diphenyl carbazole (R2=1,8- diphenyl), 9- (4- bromophenyl) -1- phenyl carbazole (R2=1- phenyl), 9- (4- bromophenyl)- 1- diphenyl sulfide carbazole (R2=1- thiophenyl), one kind of 9- (4- bromophenyl) -1.2.3.4- tetrahydro carbazole, dosage is 2.0 equivalents To 5.0 equivalents (relative to primary amino-compound I, similarly hereinafter)；
Substrate III is quinolyl triarylamine, and the nitrogen-atoms of quinoline amino is connected with the contraposition of the phenyl ring of two molecule carbazole derivates；
Synthetic method is characterized in that, using substituted 8- amido quinolines I and bromo carbazole class compound II as substrate, is added Enter the Raney nickel that molar fraction is 1% to 30%, the alkali of 1-5 molar equivalent, common organic solvents are solvent, nitrogen atmosphere Under, reaction mixture is stirred to react 1-48 hours at 25 DEG C to 160 DEG C, and saturated ammonium chloride solution is added after fully reacting and is quenched, It is extracted with polar organic solvent, anhydrous sodium sulfate is added or anhydrous magnesium sulfate is dry, through Rotary Evaporators concentration, column chromatography point From obtaining target product triarylamine compound III.
2. preparation method according to claim 1, which is characterized in that the reaction dissolvent is tetrahydrofuran, dimethyl Asia Sulfone, N-Methyl pyrrolidone, n,N-Dimethylformamide, n,N-dimethylacetamide, one kind of toluene, paraxylene, acetonitrile.
3. preparation method according to claim 1, which is characterized in that Raney nickel used is nickel fluoride, nickel chloride, bromination Nickel, nickel acetate, nickel sulfate, nickel acetate, trifluoroacetic acid nickel, trifluoromethanesulfonic acid nickel, nickel acetylacetonate, (1,1'- bis- (diphenylphosphines) Ferrocene) Nickel Chloride, double-(1,5- cyclo-octadiene) nickel (Ni (COD)2) one kind, dosage be 1% to 30% mole.
4. preparation method according to claim 1, which is characterized in that the alkali be potassium carbonate, sodium carbonate, saleratus, One kind of sodium bicarbonate, cesium carbonate, sodium tert-butoxide, potassium tert-butoxide, dosage are 2-5 equivalent.
5. preparation method according to claim 1, which is characterized in that the reaction condition is in 25-160 DEG C of reaction 1-48 Hour.
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