CN111471044B - Synthesis method of palladium-catalyzed 3-aryl 7-azaindole compound - Google Patents
Synthesis method of palladium-catalyzed 3-aryl 7-azaindole compound Download PDFInfo
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Abstract
A synthesis method of a palladium-catalyzed 3-aryl 7-azaindole compound comprises the steps of adding a 7-azaindole compound and an arylboronic acid compound into a reaction tube, adding a transition metal palladium catalyst, an oxidant, an alkali and a solvent, and reacting at 40-100 ℃ for 2-24 hours to obtain the 3-aryl 7-azaindole compound. In the invention, the reaction system does not need to be added with N-containing and P-containing ligands; in the invention, the protecting group at the N1 position in the 7-azaindole compound is not important, the existence of the protecting group does not have obvious influence on the activity and selectivity of the arylation reaction, and the reaction can selectively occur at the C3 position of the 7-azaindole compound; the invention uses arylboronic acid compounds as arylating reagents, so that the toxicity is obviously reduced, and halide with high pollution is not generated in the reaction process; the whole reaction process is simple, efficient, low in toxicity and convenient to operate.
Description
Technical Field
The invention relates to the field of organic synthesis, in particular to a synthesis method of a palladium-catalyzed 3-aryl 7-azaindole compound.
Background
7-azaindole (1H-pyrrolo [2, 3-b)]Pyridine) is an important class of aromatic organificationCompounds whose molecular structure is present extensively in the core backbone of natural products and biologically active compounds. As derivatives thereof, 3-aryl-7-azaindoles have high biological activity (L.H.Franco, et.al.J.Nat.Prod.1998,61,1130; N.B.Perry, et.al.tetrahedron 1994,50, 3987; G.Trimuluu, et.al.tetrahedron 1994,50, 3993). For example, the compound Variolin B, also known as Meriolin 1, exhibits good inhibitory properties against kinases and human cancer cell lines, IC against colon cancer HCT116 and ovarian cancer A278050Values (i.e. concentrations required to reduce cell proliferation by 50%) were as low as 0.18mM and 0.14mM, respectively (a. echalier, et. al. j. med. chem.2008,51,737). Therefore, the compounds have wide application prospect.
Review literature, there are two general routes to the synthesis of 3-aryl-7-azaindoles, the first being via intramolecular (s.llona-Minguez, et.al.chem.eur.j.2015,21,7394) or intermolecular (t.bzeih, et.al.chem.commu.2016, 52,13027) cyclization under specific catalytic conditions, and the second being a C-C coupling reaction with 7-azaindole as a substrate under transition metal catalytic conditions.
For the second method, researchers have previously mainly used brominated aromatic hydrocarbons (Patent, repub. korean Kongkae Taeho Kongbo, KR 2015017260,16Feb 2015) or arylhydrazines (y. chen, et. al. adv. synth. catal.2013,355,711) as arylating agents under transition metal catalysis in 1, 10-phenanthroline (1,10-phen), 2 '-bipyridine (2, 2' -bipy) or triphenylphosphine (PPh)3) And the 3-position arylation reaction of the substrate molecule is realized under the assistance of N, P ligand. It is noted that in the preparation process of the target compound, 7-azaindole and iodinating reagent N-iodosuccinimide (NIS) can be subjected to 3-position iodination reaction under the action of strong base, and then subjected to cross-coupling reaction with aryl boronic acid compounds (g.qian, et al.
As described above, in the conventional reports, a highly toxic coupling reagent such as an arylhydrazine compound or a halogenated (Br or I) aromatic hydrocarbon is generally used, and a highly polluting halide is produced as a byproduct, and a ligand such as N, P is often added to the reaction system to promote the reaction, and some reaction conditions are severe and even need to be performed under anhydrous and anaerobic conditions, so that it is very important to develop a simple, efficient and low-toxic method for preparing a 3-aryl-7-azaindole compound.
Disclosure of Invention
The invention aims to provide a palladium-catalyzed synthesis method of a 3-aryl 7-azaindole compound, which is simple to operate and easy to control.
In order to achieve the purpose, the invention adopts the following technical scheme:
a synthesis method of a palladium-catalyzed 3-aryl 7-azaindole compound comprises the steps of adding a 7-azaindole compound and an arylboronic acid compound into a reaction tube, adding a transition metal palladium catalyst, an oxidant, an alkali and a solvent, and reacting at 40-100 ℃ for 2-24 hours to obtain the 3-aryl 7-azaindole compound.
In a further improvement of the invention, the 7-azaindole compound is 7-azaindole, 1-phenyl-7-azaindole or 1-benzyl-7-azaindole.
The invention is further improved in that the aryl boric acid compound is phenylboronic acid, 2-methylphenylboronic acid, 3-methylphenylboronic acid, 4-methylphenylboronic acid, 3-fluorophenylboronic acid, 4-chlorophenylboronic acid or 4-methoxyphenylboronic acid.
In a further development of the invention, the transition metal palladium catalyst is Pd (OAc)2、PdCl2Or Pd (TFA)2。
In a further development of the invention, the oxidizing agent is AgOAc, Cu (OAc)2、PhI(OAc)2Or Cu (OTf)2。
In a further development of the invention, the base is Cs2CO3Or K2CO3。
A further improvement of the invention is that the solvent is N-methylpyrrolidone, dimethylacetamide, toluene or mesitylene.
In a further development of the invention, the ratio of the amounts of substance of the 7-azaindole compounds to the arylphenylboronic acid compounds is 1: (1-3); the mass ratio of the 7-azaindole compound to the transition metal palladium catalyst is 1: (0.05-0.5); the mass ratio of the 7-azaindole compound to the oxidant is 1: (1-2); the mass ratio of the 7-azaindole compound to the base is 1: (1-2).
The invention is further improved in that when the amount of the 7-azaindole compound is 0.2mmol, the amount of the solvent is 1-2 mL.
Compared with the prior art, the invention has the following beneficial effects: the reaction mechanism of the invention is as follows: firstly activating a transition metal palladium catalyst by alkali to obviously enhance the electrophilic performance of the catalyst, then carrying out electrophilic reaction on the activated catalyst at the C3 site with higher electron cloud density of the 7-azaindole compound under the action of an oxidant to generate a 7-azaindole active intermediate, then carrying out addition reaction on the intermediate and an arylphenylboronic acid compound, and then carrying out reduction elimination under the action of alkali to finally obtain an arylation product at the C3 site of the 7-azaindole; in the invention, any ligand such as N, P is not required to be added; in the invention, the protecting group at the N1 position in the 7-azaindole compound is not important, the existence of the protecting group does not have obvious influence on the activity and selectivity of the arylation reaction, and the reaction can selectively occur at the C3 position of the 7-azaindole compound; compared with the prior aryl hydrazine compounds, halogenated aromatic hydrocarbons and the like, the aryl boric acid compound has obviously reduced toxicity and does not generate high-polluting halide in the reaction process; the whole reaction process is simple, efficient, low in toxicity and convenient to operate; the synthetic route has strong selectivity and high synthetic efficiency; the reaction raw materials are cheap and easy to obtain; has wide potential application prospect.
Detailed Description
In order to further understand the present invention, the following examples are further illustrated, which are only used for explaining the present invention and are not to be construed as limiting the scope of the present invention.
In the invention, a 7-azaindole compound and a phenylboronic acid compound are used as raw materials, a transition metal palladium salt is used as a catalyst, a certain amount of oxidant, alkali and solvent are added, and the reaction is carried out for a certain time at a certain temperature to obtain an arylation product at the C3 position of the 7-azaindole.
The reaction equation of a palladium-catalyzed synthesis method of a 3-aryl 7-azaindole compound is as follows:
adding a 7-azaindole compound and an arylboronic acid compound into a reaction tube, adding a transition metal palladium catalyst, an oxidant, an alkali and a solvent, reacting for 2-24 hours at 40-100 ℃, and performing aftertreatment to obtain a C3 arylation product of the 7-azaindole.
Wherein the 7-azaindole compound is 7-azaindole, 1-phenyl-7-azaindole or 1-benzyl-7-azaindole; the arylboronic acid compound is phenylboronic acid, 2-methylphenylboronic acid, 3-methylphenylboronic acid, 4-methylphenylboronic acid, 3-fluorophenylboronic acid, 4-chlorophenylboronic acid or 4-methoxyphenylboronic acid.
The catalyst is Pd (OAc)2、PdCl2And Pd (TFA)2One kind of (1).
The oxidant is AgOAc, Cu (OAc)2、PhI(OAc)2And Cu (OTf)2One kind of (1).
The alkali is Cs2CO3And K2CO3One kind of (1).
The solvent is one of N-methyl pyrrolidone (NMP), dimethyl acetamide (DMA), toluene (tolumen) and mesitylene (mesitylene).
The mass ratio of the 7-azaindole compound to the phenylboronic acid compound is 1: (1-3).
The mass ratio of the 7-azaindole compound to the catalyst is 1: (0.05-0.5).
The mass ratio of the 7-azaindole compound to the oxidant is 1: (1 to 2)
The mass ratio of the 7-azaindole compound to the base is 1: (1-2).
The amount of the solvent is 1-2 mL by taking the amount of 0.2mmol of 7-azaindole compound as a reference.
The following are specific examples
Example 1
The catalytic synthesis method comprises the following steps: to a 15mL reaction tube under an air atmosphere were added 0.2mmol of 7-azaindole, 0.2mmol of phenylboronic acid, 0.01mmol of Pd (OAc)2，0.2mmol Cu(OAc)2，0.2mmol Cs2CO3And reacting the mixture at 40 ℃ for 24 hours in 1mL of N-methylpyrrolidone, and cooling the mixture to room temperature after the reaction is finished. The mixture was diluted with water (5mL), extracted with dichloromethane (10 mL. times.3), and the organic phases combined. Washing the organic phase with saturated saline solution (5mL), adding anhydrous sodium sulfate, drying, filtering, concentrating, separating by column chromatography, purifying and separating the product by using 300-400-mesh silica gel as a stationary phase and using mixed solvents of ethyl acetate and petroleum ether in different proportions as an eluent, concentrating and drying to obtain colorless oily substances. The physical properties and characterization data of the obtained compounds are as follows:1H NMR(400MHz,Chloroform-d):δ12.53(s,1H),8.34(d,J＝5.7Hz,1H),8.00(dd,J＝7.8,1.3Hz,1H),7.93(d,J＝7.3Hz,2H),7.55(t,J＝7.7Hz,2H),7.43(t,J＝7.4Hz,1H),7.14(dd,J＝7.8,4.8Hz,1H),6.83(s,1H).13C NMR(100MHz,Chloroform-d):δ150.1,140.4,129.3,128.7,127.5,123.6,119.2,117.2,116.2,115.9,114.1ppm.HRESI-MS:[M+H]+Calcd.for C13H10N2195.0917；Found 195.0916.
example 2
The catalytic synthesis method comprises the following steps: in an air atmosphere, to 15mL0.2mmol of 7-azaindole, 0.6mmol of 2-methylphenylboronic acid and 0.1mmol of PdCl2，0.4mmolAgOAc，0.4mmol Cs2CO32mL of dimethylacetamide was reacted at 100 ℃ for 2 hours, and after the reaction was completed, the reaction mixture was cooled to room temperature. The mixture was diluted with water (5mL), extracted with dichloromethane (10 mL. times.3), and the organic phases combined. Washing the organic phase with saturated saline solution (5mL), adding anhydrous sodium sulfate, drying, filtering, concentrating, separating by column chromatography, purifying and separating the product by using 300-400-mesh silica gel as a stationary phase and using mixed solvents of ethyl acetate and petroleum ether in different proportions as an eluent, concentrating and drying to obtain colorless oily substances. The physical properties and characterization data of the obtained compounds are as follows:1H NMR(400MHz,Chloroform-d):δ12.47(s,1H),8.31(d,J＝4.7Hz,1H),7.92(dd,J＝8.5Hz,1H),7.76(d,J＝9.0Hz,1H),7.40(d,J＝9.2Hz,1H),7.35–7.33(m,2H),7.15(m,1H),6.87(s,1H),2.23(s,3H)ppm.13C NMR(100MHz,Chloroform-d):δ147.8,141.4,139.2,137.6,131.7,128.9,125.6,124.5,119.2,118.2,117.8,115.9,105.6,27.1ppm.HRESI-MS:[M+H]+Calcd.for C13H10FN2209.1073；Found 209.1074.
example 3
The catalytic synthesis method comprises the following steps: to a 15mL reaction tube under an air atmosphere were added 0.2mmol of 7-azaindole, 0.4mmol of 4-methylphenylboronic acid, 0.02mmol of Pd (TFA)2，0.2mmol PhI(OAc)2，0.2mmol K2CO3The reaction was carried out at 80 ℃ for 12 hours in 1mL of toluene, and after completion of the reaction, the reaction mixture was cooled to room temperature. The mixture was diluted with water (5mL), extracted with dichloromethane (10 mL. times.3), and the organic phases combined. Washing the organic phase with saturated saline solution (5mL), adding anhydrous sodium sulfate, drying, filtering, concentrating, separating by column chromatography, purifying and separating the product by using 300-400-mesh silica gel as a stationary phase and using mixed solvents of ethyl acetate and petroleum ether in different proportions as an eluent, concentrating and drying to obtain colorless oily substances. Obtained chemical combinationPhysical properties and characterization data of the material were as follows:1H NMR(400MHz,Chloroform-d):δ12.52(s,1H),8.35(d,J＝4.7Hz,1H),7.91(dd,J＝8.0Hz,2H),7.78(d,J＝9.4Hz,2H),7.33(m,1H),7.13(m,1H),6.92(s,1H),2.34(s,3H)ppm.13C NMR(100MHz,Chloroform-d):δ149.1,142.4,138.7,131.7,128.9,123.6,122.5,118.2,117.2,115.9,114.6,21.3ppm.HRESI-MS:[M+H]+Calcd.for C13H10FN2209.1073；Found 209.1075.
example 4
The catalytic synthesis method comprises the following steps: to a 15mL reaction tube under an air atmosphere were added 0.2mmol of 7-azaindole, 0.4mmol of 3-fluorobenzeneboronic acid, 0.01mmol of Pd (OAc)2，0.2mmol Cu(OTf)2，0.2mmol Cs2CO3The reaction was carried out at 80 ℃ for 16 hours in 1mL of mesitylene, and after the reaction was completed, the reaction mixture was cooled to room temperature. The mixture was diluted with water (5mL), extracted with dichloromethane (10 mL. times.3), and the organic phases combined. Washing the organic phase with saturated saline solution (5mL), adding anhydrous sodium sulfate, drying, filtering, concentrating, separating by column chromatography, purifying and separating the product by using 300-400-mesh silica gel as a stationary phase and using mixed solvents of ethyl acetate and petroleum ether in different proportions as an eluent, concentrating and drying to obtain colorless oily substances. The physical properties and characterization data of the obtained compounds are as follows:1H NMR(400MHz,Chloroform-d):δ12.80(s,1H),8.36(s,1H),8.01(d,J＝7.7Hz,1H),7.68(dd,J＝23.0,8.7Hz,2H),7.51(d,J＝6.2Hz,1H),7.21–7.07(m,2H),6.84(s,1H).13C NMR(100MHz,Chloroform-d):δ163.5,149.4,142.1,138.7,128.3,127.5,123.3,121.8,118.2,117.2,115.9,115.1,112.5ppm.HRESI-MS:[M+H]+Calcd.for C13H10FN2213.0823；Found 213.0825.
example 5
The catalytic synthesis method comprises the following steps: to a 15mL reaction tube under an air atmosphere were added 0.2mmol of 7-azaindole, 0.6mmol of 4-fluorobenzeneboronic acid, 0.02mmol of Pd (OAc)2，0.4mmol Cu(OTf)2，0.2mmol Cs2CO32mL of toluene was reacted at 50 ℃ for 18 hours, and after the reaction was completed, the reaction mixture was cooled to room temperature. The mixture was diluted with water (5mL), extracted with dichloromethane (10 mL. times.3), and the organic phases combined. Washing the organic phase with saturated saline solution (5mL), adding anhydrous sodium sulfate, drying, filtering, concentrating, separating by column chromatography, purifying and separating the product by using 300-400-mesh silica gel as a stationary phase and using mixed solvents of ethyl acetate and petroleum ether in different proportions as eluents, concentrating and drying to obtain yellow oily matter. The physical properties and characterization data of the obtained compounds are as follows:1H NMR(400MHz,Chloroform-d):δ12.82(s,1H),8.36(d,J＝4.7Hz,1H),7.94(dd,J＝8.3Hz,2H),7.76(d,J＝9.6Hz,2H),7.71(s,1H),7.14(s,1H),6.85(s,1H).13C NMR(100MHz,Chloroform-d):δ160.4,149.1,142.4,138.7,129.3,128.9,123.6,118.2,117.2,115.9,112.1ppm.HRESI-MS:[M+H]+Calcd.for C13H10FN2213.0823；Found 213.0823.
example 6
The catalytic synthesis method comprises the following steps: to a 15mL reaction tube under an air atmosphere were added 0.2mmol of 7-azaindole, 0.4mmol of 4-fluorobenzeneboronic acid, 0.02mmol of Pd (OAc)2，0.2mmol Cu(OTf)2，0.2mmol Cs2CO3The reaction was carried out at 80 ℃ for 14 hours in 1mL of toluene, and after completion of the reaction, the reaction mixture was cooled to room temperature. The mixture was diluted with water (5mL), extracted with dichloromethane (10 mL. times.3), and the organic phases combined. Washing the organic phase with saturated saline solution (5mL), adding anhydrous sodium sulfate, drying, filtering, concentrating, separating by column chromatography, purifying and separating the product by using 300-400 mesh silica gel as a stationary phase and using mixed solvents of ethyl acetate and petroleum ether in different proportions as eluents, and concentratingDrying to obtain yellow oily matter. The physical properties and characterization data of the obtained compounds are as follows:1H NMR(400MHz,Chloroform-d):δ12.42(s,1H),8.34(d,J＝4.8Hz,1H),7.98(dd,J＝9.3Hz,2H),7.76(d,J＝8.6Hz,2H),7.75(s,1H),7.14(s,1H),6.55(s,1H).13C NMR(100MHz,Chloroform-d):δ149.1,142.4,138.7,129.3,128.9,128.3,123.6,118.2,117.2,115.9,112.1ppm.HRESI-MS:[M+H]+Calcd.for C13H10ClN2229.0527；Found 229.0526.
example 7
The catalytic synthesis method comprises the following steps: to a 15mL reaction tube under an air atmosphere were added 0.2mmol of 7-azaindole, 0.4mmol of 4-methoxyphenylboronic acid, 0.01mmol of Pd (OAc)2，0.2mmol Cu(OTf)2，0.2mmol Cs2CO3The reaction was carried out at 80 ℃ for 10 hours in 1mL of toluene, and after completion of the reaction, the reaction mixture was cooled to room temperature. The mixture was diluted with water (5mL), extracted with dichloromethane (10 mL. times.3), and the organic phases combined. Washing the organic phase with saturated saline solution (5mL), adding anhydrous sodium sulfate, drying, filtering, concentrating, separating by column chromatography, purifying and separating the product by using 300-400-mesh silica gel as a stationary phase and using mixed solvents of ethyl acetate and petroleum ether in different proportions as eluents, concentrating and drying to obtain yellow oily matter. The physical properties and characterization data of the obtained compounds are as follows:1H NMR(400MHz,Chloroform-d):δ12.61(s,1H),8.39(d,J＝4.4Hz,1H),7.94(dd,J＝8.3Hz,2H),7.76(d,J＝9.6Hz,2H),7.33(m,1H),7.15(m,1H),6.87(s,1H),3.87(s,3H)ppm.13C NMR(100MHz,Chloroform-d):δ147.8,141.4,137.6,131.7,128.9,125.6,124.5,119.2,118.2,115.9,105.6,57.3ppm.HRESI-MS:[M+H]+Calcd.for C14H13N2O225.1022；Found 225.1022.
example 8
The catalytic synthesis method comprises the following steps: to a 15mL reaction tube under an air atmosphere were added 0.2mmol of 1-phenyl-7-azaindole, 0.6mmol of 4-fluorobenzeneboronic acid, 0.02mmol of Pd (OAc)2，0.2mmol Cu(OTf)2，0.2mmol Cs2CO3The reaction was carried out at 80 ℃ for 12 hours in 1mL of toluene, and after completion of the reaction, the reaction mixture was cooled to room temperature. The mixture was diluted with water (5mL), extracted with dichloromethane (10 mL. times.3), and the organic phases combined. Washing the organic phase with saturated saline solution (5mL), adding anhydrous sodium sulfate, drying, filtering, concentrating, separating by column chromatography, purifying and separating the product by using 300-400-mesh silica gel as a stationary phase and using mixed solvents of ethyl acetate and petroleum ether in different proportions as eluents, concentrating and drying to obtain yellow oily matter. The physical properties and characterization data of the obtained compounds are as follows:1H NMR(400MHz,Chloroform-d):δ8.31(d,J＝4.5Hz,1H),7.92(dd,J＝8.0Hz,1H),7.56(d,J＝7.3Hz,2H),7.50(d,J＝7.3Hz,2H),7.38(t,J＝7.4Hz,1H)7.30(d,J＝8.2Hz,2H),7.20(s,1H),7.15(m,2H),6.87(s,1H),5.54(s,2H)ppm.13C NMR(100MHz,Chloroform-d):δ162.9,148.0,142.4,137.6,130.7,129.3,128.3,122.9,125.6,121.5,120.7,119.2,116.8,115.9ppm.HRESI-MS:[M+H]+Calcd.for C19H14FN2289.1136；Found 289.1135.
example 9
The catalytic synthesis method comprises the following steps: to a 15mL reaction tube under an air atmosphere were added 0.2mmol of 1-benzyl-7-azaindole, 0.6mmol of 4-fluorobenzeneboronic acid, 0.02mmol of Pd (OAc)2，0.4mmol Cu(OTf)2，0.2mmol Cs2CO32mL of toluene was reacted at 80 ℃ for 4 hours, and after the reaction was completed, the reaction mixture was cooled to room temperature. The mixture was diluted with water (5mL), extracted with dichloromethane (10 mL. times.3), and the organic phases combined. Washing the organic phase with saturated saline (5mL), adding anhydrous sodium sulfate, drying, filtering, concentrating, separating by column chromatography, and separating with 300-400 mesh silica gelThe product is purified and separated by using mixed solvents of ethyl acetate and petroleum ether with different proportions as eluent, and is concentrated and dried to obtain yellow oily matter. The physical properties and characterization data of the obtained compounds are as follows:1H NMR(400MHz,Chloroform-d):δ8.30(d,J＝4.9Hz,1H),8.00(dd,J＝8.0Hz,1H),7.66(d,J＝7.3Hz,2H),7.58(t,J＝7.4Hz,1H),7.50(d,J＝7.3Hz,2H),7.40(d,J＝9.2Hz,2H),7.20(s,1H),7.15(m,2H),6.87(s,1H)ppm.13C NMR(100MHz,Chloroform-d):δ162.9,148.0,142.4,137.6,130.7,129.3,128.3,122.9,125.6,121.5,120.7,119.2,116.8,115.9ppm.HRESI-MS:[M+H]+Calcd.for C20H16FN2303.1292；Found 303.1293.
example 10
Adding 7-azaindole and 3-methylphenylboronic acid into a reaction tube, wherein the amount of substances of the 7-azaindole is 0.2mol, and the ratio of the amounts of the substances is 1: 2, adding a catalyst, an oxidant and alkali, and reacting for 8 hours at 100 ℃ to obtain a C3-site arylation product, namely a 3-aryl 7-azaindole compound;
wherein the solvent is N-methyl pyrrolidone, and the dosage of the N-methyl pyrrolidone is 2 mL.
The catalyst is Pd (TFA)2The mass ratio of the 7-azaindole to the catalyst is 1: 0.3.
the oxidant is AgOAc, the mass ratio of the 7-azaindole to the oxidant is 1: 1.5.
the alkali is Cs2CO3The mass ratio of the 7-azaindole to the base is 1: 2.
the foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, modifications and decorations can be made without departing from the core technology of the present invention, and the modifications and decorations shall also fall within the scope of the patent protection of the present invention. Any changes which come within the meaning and range of equivalency of the claims are to be embraced within their scope.
Claims (4)
1. A synthesis method of a palladium-catalyzed 3-aryl 7-azaindole compound is characterized by comprising the steps of adding a 7-azaindole compound and an arylboronic acid compound into a reaction tube, adding a transition metal palladium catalyst, an oxidant, an alkali and a solvent, and reacting at 40-100 ℃ for 2-24 hours to obtain a 3-aryl 7-azaindole compound;
the 7-azaindole compound is 7-azaindole, 1-phenyl-7-azaindole or 1-benzyl-7-azaindole;
the arylboronic acid compound is phenylboronic acid, 2-methylphenylboronic acid, 3-methylphenylboronic acid, 4-methylphenylboronic acid, 3-fluorophenylboronic acid, 4-chlorophenylboronic acid or 4-methoxyphenylboronic acid;
the transition metal palladium catalyst is Pd (OAc)2、PdCl2Or Pd (TFA)2；
The oxidant is AgOAc, Cu (OAc)2、PhI(OAc)2Or Cu (OTf)2；
The alkali is Cs2CO3Or K2CO3。
2. The palladium-catalyzed synthesis method of a 3-aryl 7-azaindole compound according to claim 1, wherein the solvent is N-methylpyrrolidone, dimethylacetamide, toluene, or mesitylene.
3. The palladium-catalyzed method of synthesizing a 3-aryl 7-azaindole compound according to claim 1, wherein: the mass ratio of the 7-azaindole compound to the arylphenylboronic acid compound is 1: (1-3); the mass ratio of the 7-azaindole compound to the transition metal palladium catalyst is 1: (0.05-0.5); the mass ratio of the 7-azaindole compound to the oxidant is 1: (1-2); the mass ratio of the 7-azaindole compound to the base is 1: (1-2).
4. The palladium-catalyzed method of synthesizing a 3-aryl 7-azaindole compound according to claim 1, wherein: when the amount of the 7-azaindole compound is 0.2mmol, the amount of the solvent is 1-2 mL.
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