Method for preparing deuterated 2-phenylpyridine compound through catalysis of Beta zeolite supported Pd

Abstract

The invention belongs to the technical field of synthesis of deuterated compounds, discloses a method for preparing a deuterated 2-phenylpyridine compound through catalysis of Beta zeolite supported Pd, and aims at solving the technical problems that an existing deuterated method is harsh in reaction condition, expensive in deuteration reagent, tedious in preparation process and low in selectivity. The method comprises the following steps: adding a 2-phenylpyridine compound, a Pd / Beta catalyst, an oxidizing agent, a solvent and deuterium water into reaction equipment, and reacting in an air atmosphere under a heating condition; performing rotary evaporation; and separating and purifying to obtain the 2-phenylpyridine compound. The reaction has high yield and good deuteration rate, cheap D2O is used as a deuterium source, high-regioselectivity deuteration of the 2-phenylpyridine compound can be completed by using a trace amount of catalyst, the reaction is environment-friendly and efficient, the operation method is simple, the reaction condition is mild, and the catalyst is easy to separate and reuse.

Description

Technical Field

[0001] The present invention belongs to the technical field of deuterated compound synthesis, and particularly relates to a deuteration reaction of compounds containing phenylpyridine by using deuterated water as a deuterium source under the action of a Pd / Beta catalyst. Technical Background

[0002] Deuterium-labeled compounds have extensive applications in the fields of chemistry, clinical, pharmaceutical, and spectroscopic research. Therefore, the development of an efficient and selective deuterium-labeling method has attracted considerable interest among scientific researchers. The potential of deuterated drugs in improving pharmacokinetics, enhancing efficacy, or reducing toxicity and side effects has been demonstrated, stimulating more clinical studies on deuterated candidate drugs and making the demand for simple and efficient deuterium-labeling methods more urgent.

[0003] Among various deuteration methods, hydrogen-deuterium (H / D) exchange is a commonly used method, in which the hydrogen atom on a specific C-H bond in a candidate compound is replaced by deuterium to form a C-D bond, obtaining a deuterated compound. Existing H / D exchange methods mainly include acid- or base-catalyzed H / D exchange and transition-metal-catalyzed H / D exchange. However, traditional acid- or base-catalyzed methods often require harsh reaction conditions (such as high temperature, strong acid / strong base environment) and have poor tolerance to sensitive functional groups in the molecule, limiting their application scope.

[0004] Transition-metal (such as palladium, platinum, iridium, ruthenium, rhodium, etc.)-catalyzed H / D exchange can solve the above problems and has the prominent advantages of wide substrate compatibility and high deuteration selectivity. Therefore, various transition metals are widely used in the deuteration of 2-phenylpyridine compounds. However, in all methods, not only complex metal coordination compounds are required, but also some expensive organic deuterated reagents are used, which do not meet the requirements of the current green and economic deuteration synthesis method. Therefore, from the perspective of sustainability and greenness, the development of a simple catalytic system for selective deuteration of arenes / heteroarenes is very important for promoting the development of deuteration in actual industries.

[0005] However, in the deuteration of 2-phenylpyridine compounds, there are still some challenges in the prior art. Many reported methods rely on structurally complex homogeneous organometallic complexes as catalysts, which are often difficult to prepare, costly, and difficult to recycle. In addition, the commonly used deuterium sources are usually expensive organic deuterated reagents, such as deuterated solvents (e.g., deuterated benzene, deuterated toluene, such as the method for deuterating benzanthracene reported in CN202410519131.4), deuterium gas, or organosilicon deuterium reagents, etc. These reagents not only increase the production cost, but their use and handling may also bring safety and environmental problems, and do not fully meet the requirements of current chemical synthesis for green, economical, and sustainable development. For example, CN202410519131.4 discloses a method for realizing the deuteration of benzanthracene using supported noble metal catalysts such as Pt / Al2O3, Pd / Al2O3, Pt / C, or Pd / C in the presence of organic deuterated reagents such as deuterated benzene and deuterated toluene at a relatively high temperature (e.g., >160 °C) and in an inert atmosphere. This method not only relies on expensive organic deuterium sources, the reaction conditions are relatively harsh, and usually non-selective deuterated products are obtained. This indicates that for some substrates, even when using supported noble metal catalysts, it is still necessary to rely on reactive organic deuterium sources and relatively high energy input to achieve H / D exchange.

[0006] On the other hand, CN202111003892.7 reports a method for preparing deuterated benzene compounds using noble metals supported on activated carbon (such as Pd / C) and deuterium water (D2O) as the deuterium source. Although inexpensive and readily available deuterium water is used, this method usually gives fully deuterated or non-selective deuterated products, and may require specific additives (such as isopropanol) or an inert atmosphere, and its reaction mechanism is different from the selective deuteration mechanism expected by the present invention.

[0007] In particular, for the substrates with a directing group in the present invention, achieving highly regioselective deuteration is an important goal, but it still faces challenges to realize such selective transformation using simple and inexpensive D2O as the deuterium source and heterogeneous catalysts. This generally requires the catalyst to not only effectively activate the target C-H bond, but also be able to effectively activate relatively inert D2O and couple the two efficiently. Currently, the catalyst lacks the precise active site structure, electronic properties, or synergistic effect with the substrate required to achieve this specific selective transformation.

[0008] Therefore, there is an urgent need to develop a simple, efficient, and highly selective heterogeneous catalytic system that can use inexpensive and readily available deuterium water (D2O) as the sole deuterium source to achieve the deuteration reaction at a specific position (the H in the C-H bond adjacent to N in the pyridine ring) of 2-phenylpyridine compounds under mild conditions, and the catalyst should be easy to separate and reuse. Summary of the Invention

[0009] In view of the above deficiencies of the prior art, the present invention has developed a heterogeneous catalytic system: for the first time, Beta zeolite molecular sieve is used as a carrier to load palladium metal (Pd / Beta), and it is applied to the deuteration reaction of 2-phenylpyridine compounds using D2O as the deuterium source. By utilizing the characteristics of the Pd / Beta catalyst that it can not only provide the dispersion of Pd species but also modulate the electronic and geometric properties of Pd species, the Pd / Beta is used in the deuteration reaction of 2-phenylpyridine compounds, and the H in the C-H bond adjacent to N in the pyridine ring of the 2-phenylpyridine compound is successfully selectively deuterated.

[0010] The characteristics of the present invention are as follows: ① Pd / Beta can be reused, which improves the utilization efficiency of Pd; ② Using inexpensive D2O as the deuterium source, under relatively mild conditions (such as <150 °C), the cost is low; ③ Selective deuteration of 2-phenylpyridine compounds.

[0011] To achieve the above object, the technical solution adopted by the present invention is as follows:

[0012] Add the 2-phenylpyridine compound, oxidant, Pd / Beta catalyst, solvent and deuterium water into a reaction tube, react at the set reaction temperature. After the reaction is completed, the crude product is obtained by centrifugal separation, extraction and rotary evaporation, and then the deuterated 2-phenylpyridine compound is obtained by separation and purification using thin layer chromatography.

[0013]

[0014] R is independently selected from one of hydrogen, alkyl (-CH3), alkoxy (-OCH3), halogen (Cl, Br), aldehyde group (-CHO); the R group is located at the ortho or para position of the benzene ring.

[0015] In the present invention, the reaction temperature is 120 - 150 °C, and the reaction time is 12 - 48 h.

[0016] In the present invention, the oxidant used is tert-butyl hydroperoxide, iodobenzene diacetate and benzoyl peroxide, and preferably tert-butyl hydroperoxide.

[0017] In the present invention, the solvent used is 1,2-dichlorohexane, 1,2-dichloromethane, and preferably 1,2-dichlorohexane.

[0018] In the present invention, the loading amount of Pd in the Pd / Beta catalyst is 1 - 8 wt.%, preferably 2 - 4%.

[0019] In the present invention, the preparation method of the Pd / Beta catalyst is the ion exchange method.

[0020] Further, the synthesis method of Beta zeolite is as follows: Dissolve NaOH and NaAlO2 in water, add tetraethylammonium hydroxide (TPAOH), and stir the mixture at room temperature. Subsequently, add silica gel to the solution and stir to obtain an aluminosilicate gel. The gel composition of the system is Al2O3: 1.8 - 2.2, Na2O: 16 - 17, SiO2: 2.1, TPAOH: 309, H2O; transfer the gel to a crystallization kettle and perform static crystallization at 140 °C for 6 days. The obtained solid product is filtered, dried, and calcined at 550 °C for 4 hours to remove the organic template, obtaining Beta zeolite.

[0021] Preferably: Further obtain Pd / Beta zeolite by the ion exchange method: Add Pd(NO3)2 to H2O, then add Beta zeolite, stir at room temperature for 3 days, and place it in an oven at 50 °C to dry for 3 days.

[0022] In the present invention, the molar ratio of the 2-phenylpyridine compound to the oxidant is 1: 0.5 - 3, preferably 1: 0.5 - 2.

[0023] In the present invention, the molar amount of the 2-phenylpyridine compound to the mass of the Pd / Beta catalyst is 1 mol: (80 - 300) g, preferably 1 mol: (100 - 200) g.

[0024] In the present invention, the concentration of the 2-phenylpyridine compound in the solvent is 0.14 mol / L to 0.5 mol / L.

[0025] In the present invention, the molar ratio of the 2-phenylpyridine compound to the volume of deuterated water is 1 mol: (2 - 7) L, preferably 1 mol: (4 - 6) L.

[0026] Compared with the prior art, the present invention has the following beneficial effects:

[0027] (1) The present invention reports for the first time the use of a Pd / Beta heterogeneous catalyst to achieve the deuteration reaction of 2-phenylpyridine compounds. Compared with the homogeneous metal complex catalysts commonly used in the prior art, the Pd / Beta catalyst of the present invention does not require complex organic ligands, simplifying the reaction system;

[0028] (2) The present invention uses inexpensive deuterated water reagent and, under the Pd / Beta catalyst, achieves high-selectivity deuteration at specific positions (C2 and C6 positions) of 2-phenylpyridine compounds under relatively mild conditions (120 - 150 °C). Description of the Drawings

[0029] Figure 1 1H-nuclear magnetic resonance spectrum of the deuterated 2-phenylpyridine obtained in Example 1 1 ​Detailed Embodiments

[0030] To further understand the purpose, content, and advantages of the present invention, the following detailed description of the specific implementation embodiments of the present invention is provided. However, it should not be limited to the examples described below, and the reaction conditions should be changed according to the actual situation. Unless otherwise specified, the reagents and instruments used in the following examples are all commercially available products.

[0031] The preparation method of the Beta zeolite used in the examples is as follows:

[0032] 0.64 g of NaOH and 1.3 g of NaAlO2 were successively dissolved in 35 mL of water. After obtaining a clear solution, 12.0 mL of 25% tetraethylammonium hydroxide (TPAOH) was added, and the mixture was stirred at room temperature for 1 hour. Subsequently, 8.0 g of silica gel was added to the solution and stirred for 1 hour to obtain an aluminosilicate gel. The gel composition of the system was Al2O3:2Na2O:16.8SiO2:2.1TPAOH:309H2O. The gel was transferred to a crystallization kettle and statically crystallized at 140 °C for 6 days. The obtained solid product was filtered, dried, and calcined at 550 °C for 4 hours to remove the organic template, obtaining Beta zeolite.

[0033] Pd / Beta zeolite was further obtained by the ion exchange method. 100 mg of Pd(NO3)2 was added to 100 mL of H2O, and then 1 g of Beta zeolite was added. The exchange was carried out at room temperature for 3 days and dried in an oven at 50 °C to obtain the Pd / Beta catalyst. The actual loading amount of Pd was 1.5 wt.%.

[0034] The Pd / Beta catalyst prepared above was used in the following examples.

[0035] Example 1

[0036]

[0037] 30 mg of Pd / Beta zeolite, 0.2 mmol of 2-phenylpyridine, 0.1 mmol of tert-butyl hydroperoxide (TBHP), 1 mL of D2O, and 1 mL of 1,2-dichloroethane (DCE) were successively added to a reaction tube. After the reaction tube was tightened, it was placed in a reaction plate at 120 °C and reacted for 24 h. The reaction tube was taken out, and the organic phase was obtained by centrifugation and extraction. The organic phase was concentrated and separated by column chromatography to obtain the pure product. The yield of the deuterated product was 85%. After 1 1H NMR analysis, the deuteration rate at the C2' / C6' position of the product was 97%. The 1H spectrum data of the product are as follows:

[0038] 11H NMR (400 MHz, Chloroform-d) δ 8.62 (d, J = 5.0 Hz, 1H), 7.65 (s, 2H), 7.38 - 7.30 (m, 3H), 7.15 (s, 1H).

[0039] The solvent in Example 1 was replaced with 1,2-dichloromethane, the yield of the product was 65%, and the deuteration rate was 60%. When the solvent in Example 1 was replaced with N,N-dimethylformamide, no deuterated product was obtained.

[0040] The reaction temperature in Example 1 was lowered to 100 °C, the yield of the product was 80%, and the deuteration rate was 89%.

[0041] The reaction temperature in Example 1 was raised to 150 °C, the yield of the product was 78%, and the deuteration rate was 84%.

[0042] The reaction time in Example 1 was shortened to 12 h, the yield of the product was 79%, and the deuteration rate was 78%.

[0043] The amount of D2O in Example 1 was reduced to 0.5 mL, the yield of the product was 70%, and the deuteration rate was 86%.

[0044] The amount of TBHP in Example 1 was increased to 0.3 mmol, the yield of the product was 76%, and the deuteration rate was 94%.

[0045] The amount of TBHP in Example 1 was increased to 0.6 mmol, the yield of the product was 72%, and the deuteration rate was 92%.

[0046] The amount of TBHP in Example 1 was increased to 0.8 mmol, the yield of the product was 75%, and the deuteration rate was 82%.

[0047] The TBHP in Example 1 was replaced with 0.3 mmol of iodobenzene diacetate, the yield of the product was 63%, and the deuteration rate was 74.6%.

[0048] The TBHP in Example 1 was replaced with 0.1 mmol of benzoyl peroxide, the yield of the product was 77%, and the deuteration rate was 89%.

[0049] The Pd / Beta zeolite in Example 1 was replaced with Pd(NO3)2·H2O, the yield of the product was 74%, and the deuteration rate was 87%.

[0050] The Pd / Beta zeolite in Example 1 was replaced with PdO, the yield of the product was 73%, and the deuteration rate was 88%. When the air atmosphere in Example 1 was replaced with a nitrogen atmosphere, the yield of the product was 71%, and the deuteration rate was 85%.

[0051] Example 2

[0052]

[0053] 30 mg of Pd / Beta zeolite, 0.2 mmol of 2-(4-methylphenyl)pyridine, 0.1 mmol of TBHP, 1 mL of D2O and 1 mL of 1,2-dichloroethane (DCE) were successively added to the reaction tube. After the reaction tube was tightened, it was placed in a reaction plate at 120 °C and reacted for 24 h. The reaction tube was taken out, and the organic phase was obtained by centrifugation and extraction. The organic phase was concentrated and separated by column chromatography to obtain the pure product. The yield of the deuterated product was 80%. After 1 1H NMR analysis, the deuteration rate at the C2' / C6' position of the product was 99%. The 1H NMR data of the product are as follows: 1 1H NMR (400 MHz, Chloroform-d) δ 8.61 (d, J = 4.9 Hz, 1H), 7.72 - 7.60 (m, 2H), 7.20 (d, J = 9.5 Hz, 2H), 7.14 (s, 1H), 2.34 (s, 3H).

[0054] Example 3

[0055]

[0056] 30 mg of Pd / Beta zeolite, 0.2 mmol of 2-(4-methoxyphenyl)pyridine, 0.1 mmol of TBHP, 1 mL of D2O and 1 mL of 1,2-dichloroethane (DCE) were successively added to the reaction tube. After the reaction tube was tightened, it was placed in a reaction plate at 120 °C and reacted for 24 h. The reaction tube was taken out, and the organic phase was obtained by centrifugation and extraction. The organic phase was concentrated and separated by column chromatography to obtain the pure product. The yield of the deuterated product was 76%. After 1 1H NMR analysis, the deuteration rate at the C2' / C6' position of the product was 99%. The 1H NMR data of the product are as follows: 1 1H NMR (400 MHz, DMSO-d6) δ 8.61 (d, J = 3.9 Hz, 1H), 7.85 (s, 1H), 7.80 (s, 1H), 7.26 (s, 1H), 7.03 (s, 2H), 3.80 (s, 3H).

[0057] Example 4

[0058]

[0059] Add 30 mg of Pd / Beta zeolite, 0.2 mmol of 2-(4-trifluoromethylphenyl)pyridine, 0.1 mmol of TBHP, 1 mL of D2O and 1 mL of 1,2-dichloroethane (DCE) into the reaction tube in sequence. After tightening the reaction tube, place it in a reaction plate at 120 °C and react for 24 h. Take out the reaction tube, and obtain the organic phase through centrifugation and extraction. The organic phase is concentrated and separated by column chromatography to obtain the pure product. The yield of the deuterated product is 82%. After 1 1H NMR analysis, the deuteration rate at the C2' / C6' position of the product is 94%. The 1H spectrum data of the product are as follows: 1 1H NMR (400 MHz, Chloroform-d) δ 8.73 (d, J = 4.8 Hz, 1H), 7.83 - 7.69 (m, 4H), 7.28 (d, J = 13.8 Hz, 1H).

[0060] Example 5

[0061]

[0062] Add 30 mg of Pd / Beta zeolite, 0.2 mmol of 2-(4-chlorophenyl)pyridine, 0.1 mmol of TBHP, 1 mL of D2O and 1 mL of 1,2-dichloroethane (DCE) into the reaction tube in sequence. After tightening the reaction tube, place it in a reaction plate at 120 °C and react for 24 h. Take out the reaction tube, and obtain the organic phase through centrifugation and extraction. The organic phase is concentrated and separated by column chromatography to obtain the pure product. The yield of the product is 81%. After 1 1H NMR analysis, the deuteration rate at the C2' / C6' position of the deuterated product is 98%. The 1H spectrum data of the product are as follows: 1 1H NMR (400 MHz, DMSO-d6) δ 8.66 (d, J = 3.9 Hz, 1H), 7.95 (s, 1H), 7.87 (s, 1H), 7.53 (s, 2H), 7.36 (s, 1H).

[0063] Example 6

[0064]

[0065] Add 30 mg of Pd / Beta zeolite, 0.2 mmol of 3-methyl-2-phenylpyridine, 0.1 mmol of TBHP, 1 mL of D2O and 1 mL of 1,2-dichloroethane (DCE) into the reaction tube in sequence. After tightening the reaction tube, place it in a reaction plate at 120 °C and react for 24 h. Take out the reaction tube, and obtain the organic phase through centrifugation and extraction. The organic phase is concentrated and separated by column chromatography to obtain the pure product. The yield of the product is 76%. After 1 1H NMR analysis, the deuteration rate at the C2' / C6' position of the deuterated product is 98%. The 1H spectrum data of the product are as follows:1 H NMR (400MHz, DMSO-d6) δ8.61(d,J=3.9Hz,1H),7.85(s,1H),7.80(s,1H),7.26(s,1H),7.03(s,2H),3.80(s,3H).

[0066] Comparative Example 1

[0067] 30 mg PdCl2, 0.2 mmol 2-phenylpyridine, 0.1 mmol TBHP, 1 mL D2O and 1 mL 1,2-dichloroethane (DCE) were added to the reaction tube in sequence. The reaction tube was tightened and placed in a reaction plate at 120°C. The reaction was allowed to react for 24 h. The reaction tube was taken out and the organic phase was obtained by centrifugation and extraction. The organic phase was concentrated and separated by column chromatography to obtain the pure product. The yield of the product was 68%. 1 HNMR analysis showed that the deuteration rate of the product was 50%.

[0068] Comparative Example 2

[0069] Pd / Beta zeolite was further obtained by ion exchange method: 100 mg Pd(NO3)2 was added to 100 mL H2O, and then 1 g Beta zeolite was added. The mixture was exchanged at room temperature for 3 days and dried in an oven at 50°C to obtain Pd / Beta catalyst. The catalyst was then calcined at 450°C for 3 h to obtain calcined Pd / Beta.

[0070] 30 mg of Pd / Beta calcined at 450 ° C, 0.2 mmol of 2-phenylpyridine, 0.1 mmol of TBHP, 1 mL of D2O and 1 mL of 1,2-dichloroethane (DCE) were added to the reaction tube in sequence. The reaction tube was tightened and placed in a reaction plate at 120 ° C. The reaction was allowed to react for 24 h. The reaction tube was taken out and the organic phase was obtained by centrifugation and extraction. The organic phase was concentrated and separated by column chromatography to obtain the pure product. The yield of the product was 71%. 1 HNMR analysis showed that the deuteration rate of the product was 60%.

[0071] Comparative Example 3

[0072] MOR zeolite was prepared according to the reference Journal of Catalysis, 2016, 338, 210. Pd / MOR catalyst was prepared by ion exchange method. 30 mg Pd / MOR, 0.2 mmol 2-phenylpyridine, 0.1 mmol TBHP, 1 mL D2O and 1 mL 1,2-dichloroethane (DCE) were added to the reaction tube in sequence. The reaction tube was tightened and placed in a reaction plate at 120° C. The reaction was allowed to react for 24 h. The reaction tube was removed and the organic phase was obtained by centrifugation and extraction. The organic phase was concentrated and separated by column chromatography to obtain a pure product. The yield of the product was 76%.1 By \(^1\)H NMR analysis, the deuteration rate of the product was 75%.

[0073] Comparative Example 4

[0074] USY zeolite was prepared according to the reference Applied Catalysis A: General, 2012, 433 - 434, 251 - 257. The Pd / USY catalyst was prepared by the ion exchange method. 30 mg of Pd / USY, 0.2 mmol of 2-phenylpyridine, 0.1 mmol of TBHP, 1 mL of \(D_2O\) and 1 mL of 1,2-dichloroethane (DCE) were successively added into the reaction tube. After the reaction tube was tightened, it was placed in a reaction plate at 120 °C and reacted for 24 h. The reaction tube was taken out, and the organic phase was obtained by centrifugation and extraction. The organic phase was concentrated and separated by column chromatography to obtain the pure product. The yield of the product was 67%. By 1 By \(^1\)H NMR analysis, the deuteration rate of the product was 65%.

[0075] Comparative Example 6

[0076] Silicalite-1 zeolite was prepared according to the reference Journal of Catalysis, 2018, 359, 130. The Pd / Silicalite-1 catalyst was prepared by the ion exchange method. 30 mg of Pd / Silicalite-1, 0.2 mmol of 2-phenylpyridine, 0.1 mmol of TBHP, 1 mL of \(D_2O\) and 1 mL of 1,2-dichloroethane (DCE) were successively added into the reaction tube. After the reaction tube was tightened, it was placed in a reaction plate at 120 °C and reacted for 24 h. The reaction tube was taken out, and the organic phase was obtained by centrifugation and extraction. The organic phase was concentrated and separated by column chromatography to obtain the pure product. The yield of the product was 65%. By 1 By \(^1\)H NMR analysis, the deuteration rate of the product was 35%.

[0077] Comparative Example 7

[0078] 30 mg of Beta zeolite, 0.2 mmol of 2-phenylpyridine, 0.1 mmol of TBHP, 1 mL of \(D_2O\) and 1 mL of 1,2-dichloroethane (DCE) were successively added into the reaction tube. After the reaction tube was tightened, it was placed in a reaction plate at 120 °C and reacted for 24 h. The reaction tube was taken out, and the organic phase was obtained by centrifugation and extraction. The organic phase was concentrated and separated by column chromatography to obtain the pure product. The yield of the product was 0%. By 1 By \(^1\)H NMR analysis, the deuteration rate of the product was 0%, and no deuteration occurred.

[0079] Comparative Example 8

[0080] Add 30 mg of Pd / Beta, 0.2 mmol of 2-phenylpyridine, 1 mL of D2O and 1 mL of 1,2-dichloroethane (DCE) into the reaction tube in sequence. After tightening the reaction tube, place it in a reaction plate at 120 °C and react for 24 h. Take out the reaction tube, and obtain the organic phase through centrifugation and extraction. The organic phase is concentrated and separated by column chromatography to obtain the pure product. The yield of the product is 47%. After 1 1H NMR analysis, the deuteration rate of the product is 36%.

[0081] The above embodiments are only used to illustrate the technical solutions of the present invention, rather than to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, those of ordinary skill in the art should understand that: they can still modify the technical solutions recorded in the foregoing embodiments, or perform equivalent replacements on some of the technical features; and these modifications or replacements do not make the essence of the corresponding technical solutions deviate from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims

1. A method for preparing deuterated 2-phenylpyridine compounds by using Pd supported on Beta zeolite as a catalyst, which is characterized in that The method is specifically carried out according to the following steps: Mix the 2-phenylpyridine compound shown in Formula 1, deuterium water, Pd / Beta catalyst, oxidant and solvent, and carry out the reaction at a set reaction temperature to obtain the deuterated 2-phenylpyridine compound shown in Formula 2; The Pd / Beta catalyst is a heterogeneous catalyst formed by loading metallic palladium on a Beta zeolite support.

2. The method for preparing deuterated 2-phenylpyridine compounds by Pd-catalysis supported on Beta zeolite according to claim 1, wherein: R is independently selected from one of hydrogen, alkyl, alkoxy, halogen, and aldehyde group; the R group is located at the ortho or para position of the benzene ring.

3. The method for catalytically preparing deuterated 2-phenylpyridine compounds supported on Beta zeolite according to claim 1, wherein: The reaction temperature is 120 - 150 °C, and the reaction time is 12 - 48 h.

4. The method for preparing deuterated 2-phenylpyridine compounds by using Pd supported on Beta zeolite as catalyst according to claim 1, characterized in that: The oxidant is at least one of tert-butyl hydroperoxide, iodobenzene diacetate, and benzoyl peroxide.

5. The method for catalytic preparation of deuterated 2-phenylpyridine compounds supported on Beta zeolite according to claim 1, wherein: The solvent is selected from at least one of 1,2-dichloroethane and dichloromethane.

6. The method for catalytically preparing deuterated 2-phenylpyridine compounds supported on Beta zeolite according to claim 1, wherein: In the Pd / Beta catalyst, the loading amount of metallic palladium is 1 - 8 wt.%.

7. The method for preparing deuterated 2-phenylpyridine compounds by Pd-catalysis supported on Beta zeolite according to claim 1, wherein: The molar ratio of the 2-phenylpyridine compound to the oxidant is 1:(0.5 - 3).

8. The method for preparing deuterated 2-phenylpyridine compounds by Pd-catalysis supported on Beta zeolite according to claim 1, wherein: The molar amount ratio of the 2-phenylpyridine compound to the mass of the Pd / Beta catalyst is 1 mol:(80 - 300) g.

9. The method for preparing deuterated 2-phenylpyridine compounds by Pd-catalysis supported on Beta zeolite according to claim 1, wherein: The concentration of the 2-phenylpyridine compound in the solvent is 0.14 mol / L to 0.5 mol / L.

10. The method for preparing deuterated 2-phenylpyridine compounds by using Pd supported on Beta zeolite according to claim 1, wherein: The volume ratio of the added deuterium water to the molar amount of the 2-phenylpyridine compound is (2 - 7) L:1 mol.

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