CN105418491B - 一种1‑(4‑吡啶基)‑4‑(4＇‑吡啶基乙烯基)苯及其制备方法和用途 - Google Patents
一种1‑(4‑吡啶基)‑4‑(4＇‑吡啶基乙烯基)苯及其制备方法和用途 Download PDFInfo
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims abstract description 43
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 7
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 7
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 7
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 claims abstract description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 42
- 229910052763 palladium Inorganic materials 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000003426 co-catalyst Substances 0.000 claims description 2
- 230000036571 hydration Effects 0.000 claims description 2
- 238000006703 hydration reaction Methods 0.000 claims description 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 1
- -1 benzene compound Chemical class 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 abstract 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 239000003446 ligand Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- XIOUDVJTOYVRTB-UHFFFAOYSA-N 1-(1-adamantyl)-3-aminothiourea Chemical compound C1C(C2)CC3CC2CC1(NC(=S)NN)C3 XIOUDVJTOYVRTB-UHFFFAOYSA-N 0.000 description 2
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000012773 waffles Nutrition 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/127—Preparation from compounds containing pyridine rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
一种1‑(4‑吡啶基)‑4‑(4＇‑吡啶基乙烯基)苯是苯环的1‑位与一个吡啶基团的4‑位相连、苯环的4‑位与一个4‑吡啶基乙烯基团的乙烯基相连的化合物；其制备方法是首先由对溴碘苯和4‑乙烯基吡啶通过Heck反应生成中间体1‑(4‑吡啶基)‑2‑(4‑溴苯基)乙烯；然后中间体和4‑吡啶硼酸通过Suzuki反应合成目标产物1‑(4‑吡啶基)‑4‑(4′‑吡啶基乙烯基)苯。本制备方法工艺简单。反应条件温和，产率高。本1‑(4‑吡啶基)‑4‑(4′‑吡啶基乙烯基)苯化合物的用途是作为电子给予体在制备配位化合物中的应用。
Description
一.技术领域
本发明涉及一种精细化学品的制备方法和用途，特别涉及一种不对称共轭双吡啶化合物的制备方法和用途，确切地说是一种1-(4-吡啶基)-4-(4′-吡啶基乙烯基)苯的制备方法和用途。
二.背景技术
共轭化合物因具有良好的光学性质，在工业生产和日常生活中被人们广泛应用。此外，尺寸较长的刚性联吡啶化合物配位能力强、分子不易弯曲，是制备具有吸附、分离等性能的多孔配合物的优良配体。近年来，商业化的刚性双吡啶配体如4,4′-联吡啶、1,2-二(4-吡啶基)乙烯在功能配合物的合成及应用方面发挥了巨大的作用。而含有共轭基团更多、尺寸更长的双吡啶配体却少有研究。因此，设计并开发出尺寸较长的刚性双吡啶配体并将其用于组装功能配合物具有重要的科学意义和广阔应用价值。
三.发明内容
本发明的目的提供一种共轭性较强、分子尺寸较长的双吡啶配体，也就是不对称共轭双吡啶化合物，所要解决的技术问题是遴先工艺路线最短、也就是最捷径的制备方法。
本发明所称的不对称共轭双吡啶化合物是在苯环的1，4-位分别引入一个4-吡啶基团和一个4-乙烯吡啶基基团，其化学结构式如下：
本不对称共轭双吡啶化合物的制备方法，包括中间体的制备、目标产物的合成和分离，所述的中间体是1-(4-吡啶基)-2-(4-溴苯基)乙烯，其制备是对溴碘苯和4-乙烯基吡啶于N,N′-二甲基甲酰胺溶剂中在二价钯催化剂和缚酸剂三乙胺存在条件下100-110℃搅拌8-12小时以完成Heck反应。化学反应式如下：
所述的目标产物的合成是中间体1-(4-吡啶基)-2-(4-溴苯基)乙烯和4-吡啶硼酸于N,N′- 二甲基甲酰胺溶剂中在零价钯催化剂和助催化剂碳酸铯存在条件下及氮气气氛中90-110℃下搅拌22-25小时使Suzuki反应完全。化学反应式如下：
所述的分离是指中间体和目标产物自反应体系中取出并纯化。具体过程是向反应体系中加入过量的水，使中间体和目标产物分别沉淀析出，过滤、洗涤并干燥，然后进行硅胶柱层析纯化(层析柱的内径为40mm，长度为457mm；所用硅胶的规格为200-300目)，用体积比为2：1的乙酸乙酯和石油醚混合液洗脱，收集洗脱液，旋转蒸发脱溶，分别得到中间体和目标产物。
所述的二价钯催化剂是氯化钯和水合肼反应的产物。具体过程是氯化钯与过量的水合肼混合搅拌2小时，滤去多余的水合肼即是二价钯催化剂。
所述的零价钯催化剂是四(三苯基膦)钯，该催化剂中钯的价态为零价，为避免零价钯被氧化失去催化活性，该反应需要在无水无氧条件下进行。
本制备方法工艺简单，反应条件温和，产率高。
本发明制备的目标产物是一种刚性长链双吡啶共轭化合物，故共轭性较强，两端氮原子上的弧对电子易于和金属离子(即中心离子)自组装形成性能各异的配合物，是制备具有优良光学、吸附性能的配合物的优良配体。
本1-(4-吡啶基)-4-(4-吡啶基乙烯基)苯的用途是作为电子给予体即配体在制备配位化合物中的应用。
四.附图说明
图1为1-(4-吡啶基)-4-(4′-吡啶基乙烯基)苯的核磁共振氢谱图；
图2为由1-(4-吡啶基)-4-(4′-吡啶基乙烯基)苯与六水合硝酸锌制得的配合物的晶体结构图。
图3为配体和配合物的荧光发射光谱(浅色为配体，深色为配合物)。
五.具体实施方式
非限定实施例叙述为下：
对溴碘苯、4-乙烯基吡啶、氯化钯、水合肼、4-吡啶硼酸、碳酸铯、四(三苯基膦)钯均从上海百灵威化学技术有限公司购置，200-300目硅胶从青岛海洋化工厂购置，乙酸乙酯、石油醚、N,N′-二甲基甲酰胺和三乙胺从国药集团化学试剂有限公司购置。
1.二价钯催化剂的制备
将氯化钯0.18g(100mmol)与5mL浓度为50％的水合肼混合搅拌2小时左右，过滤，得到灰色固体，真空干燥后密封保存。
2.中间体的制备
将对溴碘苯5.66g(20mmol)溶于25mL的N,N′-二甲基甲酰胺中，再向其中加入二价钯催化剂35mg、4-乙烯基吡啶2.52g(24mmol)和三乙胺2.53g(25mmol)，105℃左右温度下搅拌，10小时左右反应完全。
反应停止后，向将上述的反应瓶中加入过量水，析出淡黄色的沉淀物。将此淡黄色的固体用水洗涤后干燥，然后将其进行硅胶柱层析分离，洗脱剂为乙酸乙酯：石油醚＝2：1(体积比)。将收集到的黄色溶液用旋转蒸发仪蒸去溶剂，得到淡黄色固体1-(4-吡啶基)-2-(4-溴苯基)乙烯，质量为4.37g，产率84％。
3.目标产物的合成
将1-(4-吡啶基)-2-(4-溴苯基)乙烯2.60g(10mmol)，零价钯催化剂四(三苯基膦)钯116mg(0.1mmol)、4-吡啶硼酸1.35g(11mmol)和碳酸铯3.58g(11mmol)加入100mL的Schlenk烧瓶中。用高纯氮气置换烧瓶中的空气后，再向反应体系中加入20mL的N,N′-二甲基甲酰胺，在100℃左右温度下搅拌，24小时左右反应完全。
反应停止后，向上述的反应瓶中加入过量水，析出淡黄色的沉淀物。将此淡黄色的固体用水洗涤后干燥，然后将其进行硅胶柱层析分离，洗脱剂为乙酸乙酯：石油醚＝2：1(体积比)。将收集到的黄色溶液用旋转蒸发仪蒸去溶剂，得到淡黄色固体1-(4-吡啶基)-4-(4′-吡啶基乙烯基)苯，质量为1.96g，产率76％。
对产物1-(4-吡啶基)-4-(4′-吡啶基乙烯基)苯进行了红外、元素分析、核磁共振氢谱等表征。结果如下：
红外:v(KBr)/cm-13442m,3024w,1598s,1543m,1506w,1422s,1327w,1280w,1219w,971s,866w,835s,804w,592s,556s.
元素分析(C18H14N2):理论值(％):C,83.69；H,5.46；N,10.84；实验值(％):C,83.35；H,5.51；N,10.72。
1NMR(400MHz,CDCl3,298K,TMS):δ＝8.68(d,2H,Py–H),8.61(d,2H,Py–H),7.68(q,4H,Py–H),7.54(d,2H,Ph–H),7.40(d,2H,Ph–H),7.33(d,1H,CH＝CH),7.13(d,1H,CH＝CH)。见图1。
4.配合物的制备
取六水合硝酸锌(0.15g，0.5mmol)，4,4′-二苯醚二甲酸(0.12g，0.5mmol)和1-(4-吡啶 基)-4-(4′-吡啶基乙烯基)苯(0.13g，0.5mmol)放入容量为25mL的反应瓶中，加入15mL水后封闭。将反应瓶于170℃恒温反应3天，缓慢降温至室温，得到黄色的配合物晶体。其晶体参考数如下：
配合物的晶体学参数：C102H75N9O20Zn4,Mr＝2008.27,monoclinic,space groupP21/n, α＝90.00°,β＝116.52(3°,γ＝90.00°, Z＝2,Dc＝1.427g cm-3,μ＝1.091mm-1,83162reflectionsmeasured,8259unique reflections(Rint＝0.0437),7117observed reflections(I>2σ(I)),625parameters,R1＝0.0526,wR2＝0.1419,S＝1.136。
配合物晶体的X-射线单晶图见图2。
5.配合物的荧光性能
在波长为365nm的光的激发下，配体1-(4-吡啶基)-4-(4′-吡啶基乙烯基)苯发射出波长为500nm的荧光；而配合物在相同波长光的激发下，发射波长为522nm的光。配合物的荧光发射光谱相对配体发生了明显的红移。因此，利用该配体合成的配合物可广泛用于制备发射不同颜色光的荧光材料。
配体及配合物的荧光发射光谱图见图3。
Claims (3)
1.一种1-(4-吡啶基)-4-(4′-吡啶基乙烯基)苯的制备方法，包括中间体的制备、目标产物的合成和分离，其特征在于：所述的中间体为1-(4-吡啶基)-2-(4-溴苯基)乙烯，其制备是对溴碘苯和4-乙烯基吡啶于N,N′-二甲基甲酰胺溶剂中在二价钯催化剂和缚酸剂三乙胺存在条件下、100-110℃搅拌反应8-12小时；反应结束后分离；所述的目标产物合成是中间体1-(4-吡啶基)-2-(4-溴苯基)乙烯和4-吡啶硼酸于N,N′-二甲基甲酰胺溶剂中在零价钯催化剂和助催化剂碳酸铯存在条件下及氮气气氛中、90-110℃下搅拌反应22-25小时；反应结束后分离。
2.根据权利要求1所述的制备方法，其特征在于：所述的二价钯催化剂为氯化钯和水合肼反应的产物。
3.根据权利要求1所述的制备方法，其特征在于：所述的零价钯催化剂是四(三苯基膦)钯。
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