WO2023142128A1 - Procédé de synthèse d'un composé 2-phényl-5-benzyl-imidazo[1,2-a]pyridine - Google Patents

Procédé de synthèse d'un composé 2-phényl-5-benzyl-imidazo[1,2-a]pyridine Download PDF

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WO2023142128A1
WO2023142128A1 PCT/CN2022/075264 CN2022075264W WO2023142128A1 WO 2023142128 A1 WO2023142128 A1 WO 2023142128A1 CN 2022075264 W CN2022075264 W CN 2022075264W WO 2023142128 A1 WO2023142128 A1 WO 2023142128A1
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imidazo
phenyl
benzyl
pyridine
reaction
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PCT/CN2022/075264
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Chinese (zh)
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孙宏枚
李文俊
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苏州大学
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Definitions

  • the invention belongs to the technical field of organic synthesis preparation, and in particular relates to a method for synthesizing 2-phenyl-5-benzyl-imidazo[1,2-a]pyridine compounds.
  • 2-Phenylimidazo[1,2-a]pyridine is an important nitrogen-containing heterocyclic structural unit, which exists in many natural products, drug molecules and photoelectric functional materials. Therefore, it is necessary to modify this skeleton It has important application value (see Yu, Y.; Su, Z.; Cao, H. Chem. Rec. 2019 , 19 , 2105), and there are many existing techniques for various alkylation modifications of this backbone There are many reports in the literature, but there are few reports on the use of alkenes as alkylating agents.
  • the purpose of this invention is to provide a new method for the synthesis of 2-phenyl-5-benzyl-imidazo[1,2-a]pyridine compounds, i.e. air-stable mixed-type nickel (II) complexes: Ni[P(OEt) 3 ] ⁇ [RNC(CH 3 )C(CH 3 )NR]C ⁇ Br 2 is the catalyst (R is 2,4,6-trimethylphenyl, and the molecular formula can be simplified as Ni[P (OEt) 3 ](IMes Me )Br 2 ), prepared by alkylation of arylethenes with 2-phenylimidazo[1,2-a]pyridines in the presence of sodium tert-butoxide Synthesis of 2-phenyl-5-benzyl-imidazo[1,2-a]pyridine compounds.
  • II nickel
  • the present invention adopts the following technical scheme: the application of nitrogen heterocyclic carbene mixed nickel (II) complexes as catalysts in the synthesis of 2-phenyl-5-benzyl-imidazo[1,2-a]pyridine compounds .
  • a method for synthesizing 2-phenyl-5-benzyl-imidazo[1,2-a]pyridine compounds comprising the following steps, in an inert gas atmosphere, mixing nitrogen-heterocyclic carbene group mixed type nickel (II ) complexes, additives, 2-phenylimidazo[1,2-a]pyridine compounds, arylvinyl compounds and solvents, react to obtain 2-phenyl-5-benzyl-imidazo[1,2- a] Pyridines.
  • the nitrogen heterocyclic carbene mixed nickel (II) complex is Ni(IMes Me )[P(OEt) 3 ]Br 2 , and its chemical structural formula is as follows: .
  • R is the following structural formula: .
  • the reaction is terminated with water, and the reaction product is extracted with ethyl acetate, separated and purified by column chromatography to obtain the product, which can be quantitatively analyzed.
  • the additive is tert-butoxide, preferably, the tert-butoxide is sodium tert-butoxide, potassium tert-butoxide or lithium tert-butoxide.
  • the temperature of the reaction is 80-120° C., and the time is 10-20 hours.
  • the reaction temperature is 110°C, and the reaction time is 18 hours.
  • the inert gas is argon or nitrogen;
  • the solvent is benzene solvent, ether solvent, etc., such as toluene, tetrahydrofuran, methyl tetrahydrofuran.
  • the molar ratio of nitrogen heterocyclic carbene mixed type nickel (II) complexes, additives, 2-phenylimidazo[1,2-a]pyridine compounds, and aryl vinyl compounds is (0.02 ⁇ 0.06):(0.8 ⁇ 1):1:(1 ⁇ 1.6).
  • the amount of arylethene compounds is 1.5 times that of 2-phenylimidazo[1,2-a]pyridine compounds
  • the amount of sodium tert-butoxide is 2-phenyl
  • the amount of catalyst used is 1 times that of 2-phenylimidazo[1,2-a]pyridine compounds, and the amount of catalyst is 5% of that of 2-phenylimidazo[1,2-a]pyridine compounds.
  • 2-phenylimidazo[1,2-a]pyridine compounds are expressed by the following chemical structural formula: .
  • R is one of hydrogen, methoxy or trifluoromethyl; the chemical structural formula of the aryl vinyl compound is as follows: .
  • aryl vinyl compounds include styrene, p-methylstyrene, m-methylstyrene, p-methoxystyrene, p-fluorostyrene, p-tert-butylstyrene, p-trimethylsilylbenzene Ethylene, 2,4,6-trimethylstyrene, p-dianilinostyrene, 1-vinylnaphthalene, 4-vinylbiphenyl, 2-vinylthiophene, or 2-vinyl-N-methylpyrrole .
  • R 1 is one of hydrogen, methoxy or trifluoromethyl
  • Ar comes from aryl vinyl compounds and is an aromatic group or a heterocyclic aromatic group, including phenyl, p-methylphenyl, m-methyl Phenyl, p-methoxyphenyl, p-fluorophenyl, p-tert-butylphenyl, p-trimethylsilylphenyl, 2,4,6-trimethylphenyl, p-dianilinophenyl, Naphthyl, biphenyl, thienyl or N-methylpyrrolyl.
  • the present invention uses the air-stable mixed type nickel (II) complex as a catalyzer, and realizes arylethene compound and 2 in the presence of sodium tert-butoxide -Hydroheteroarylation reaction of phenylimidazo[1,2-a]pyridine compounds, the 5-position of 2-phenylimidazo[1,2-a]pyridine skeleton can be modified by alkylation, synthesized 2-phenyl-5-benzyl-imidazo[1,2-a]pyridine compounds were obtained.
  • II air-stable mixed type nickel
  • the preparation method disclosed by the present invention has mild reaction conditions and good substrate applicability. At the same time, because the divalent nickel (II) complex has the characteristics of air stability and easy synthesis, it has practical application value.
  • R 2,4,6-tri
  • azacyclic carbene [RNC(CH 3 )C(CH 3 )NR]C (0.3325 g, 1.0 mmol) was added to bis(triethylphosphite) dibromide under argon Nickel (II) (0.5508 g, 1.0 mmol) in tetrahydrofuran solution, react at room temperature for 3 hours, remove the solvent in vacuo, wash the residue with n-hexane, extract the residue with toluene, transfer the clear liquid and remove the solvent toluene to obtain a red color
  • the solid is a divalent nickel (II) complex, called Ni[P(OEt) 3 ](IMes Me )Br 2 , and its chemical structure is as follows: R has the following structural formula: .
  • R has the following structural formula: .
  • Example Two divalent nickel (II) complexes are used as catalysts to catalyze the hydroheteroarylation reaction of styrene and 2-phenylimidazo[1,2-a]pyridine: under the protection of argon, in the reaction flask Ni[P(OEt) 3 ]( IMesMe ) Br2 catalyst (18 mg, 0.025 mmol, 5 mol%), sodium tert-butoxide (48 mg, 0.5 mmol), 2-phenylimidazo[1 ,2-a]pyridine (97mg, 0.5mmol), styrene (86 ⁇ l, 0.75mmol), toluene (1.5ml) as solvent, reacted at 110°C for 18 hours, terminated the reaction with water, and the reaction product was used Extracted with ethyl acetate, separated and purified by column chromatography (using a mixed solvent of ethyl acetate/petroleum ether with a volume ratio of 1:2 as the developing
  • Example 2 On the basis of Example 2, the solvent was adjusted from toluene to 2-MeTHF, and the rest remained unchanged, and the gas phase yield of the product was 84%.
  • Embodiment Three divalent nickel (II) complex Ni[P(OEt) 3 ](IMes Me )Br 2 is a catalyst, catalyzes the reaction of p-methylstyrene and 2-phenylimidazo[1,2-a]pyridine Hydrogen heteroarylation reaction: under the protection of argon, add catalyst (18 mg, 0.025 mmol, 5 mol%), sodium tert-butoxide (48 mg, 0.5 mmol), 2-phenylimidazole in sequence in the reaction flask And[1,2-a]pyridine (97mg, 0.5mmol), p-methylstyrene (99 ⁇ l, 0.75mmol), toluene (1.5ml) as solvent, react at 80 o C for 13 hours, The reaction was terminated with water, and the reaction product was extracted with ethyl acetate, separated and purified by column chromatography (using a mixed solvent of ethyl acetate/petroleum ether volume ratio of
  • Embodiment 4 Divalent nickel (II) complex Ni[P(OEt) 3 ](IMes Me )Br 2 is a catalyst, and catalyzes the reaction of m-methylstyrene and 2-phenylimidazo[1,2-a]pyridine Hydrogen heteroarylation reaction: under the protection of argon, add catalyst (18 mg, 0.025 mmol, 5 mol%), sodium tert-butoxide (48 mg, 0.5 mmol), 2-phenylimidazole in sequence in the reaction flask And[1,2-a]pyridine (97mg, 0.5mmol), m-methylstyrene (100 ⁇ l, 0.75mmol), toluene (1.5ml) as solvent, react at 90 o C for 16 hours, The reaction was terminated with water, and the reaction product was extracted with ethyl acetate, separated and purified by column chromatography (using a mixed solvent with a volume ratio of ethyl acetate/petrole
  • Example 5 Divalent nickel (II) complex Ni[P(OEt) 3 ](IMes Me )Br 2 is used as a catalyst to catalyze p-methoxystyrene and 2-phenylimidazo[1,2-a]pyridine Hydrogen heteroarylation reaction: under the protection of argon, the catalyst (18 mg, 0.025 mmol, 5 mol%), sodium tert-butoxide (48 mg, 0.5 mmol), 2-phenyl Imidazo[1,2-a]pyridine (97 mg, 0.5 mmol), p-methoxystyrene (100 microliters, 0.75 mmol), toluene (1.5 ml) were used as solvents, and reacted at 80 o C for 10 Hours, the reaction was terminated with water, and the reaction product was extracted with ethyl acetate, separated and purified by column chromatography (using a mixed solvent with a volume ratio of ethyl acetate/petroleum
  • Example 6 Divalent nickel (II) complex Ni[P(OEt) 3 ](IMes Me )Br 2 is a catalyst to catalyze the hydrogenation of p-fluorostyrene and 2-phenylimidazo[1,2-a]pyridine Heteroarylation reaction: under the protection of argon, the catalyst (18 mg, 0.025 mmol, 5 mol%), sodium tert-butoxide (48 mg, 0.5 mmol), 2-phenylimidazo [1,2-a]pyridine (97mg, 0.5mmol), p-fluorostyrene (89 ⁇ l, 0.75mmol), toluene (1.5ml) as solvent, react at 120 o C for 20 hours, terminate with water Reaction, the reaction product was extracted with ethyl acetate, separated and purified by column chromatography (using a mixed solvent with a volume ratio of ethyl acetate/petroleum ether of 1:2 as the developing solvent), and the yield was 89%.
  • Example 7 Divalent nickel (II) complex Ni[P(OEt) 3 ](IMes Me )Br 2 is used as a catalyst to catalyze p-tert-butylstyrene and 2-phenylimidazo[1,2-a]pyridine Hydrogen heteroarylation reaction: under the protection of argon, the catalyst (18 mg, 0.025 mmol, 5 mol%), sodium tert-butoxide (48 mg, 0.5 mmol), 2-phenyl Imidazo[1,2-a]pyridine (97 mg, 0.5 mmol), p-tert-butylstyrene (137 microliters, 0.75 mmol), toluene (1.5 ml) were used as solvents, and reacted at 90 o C for 15 Hours, the reaction was terminated with water, and the reaction product was extracted with ethyl acetate, separated and purified by column chromatography (using a mixed solvent with a volume ratio of ethyl acetate
  • Example 8 Divalent nickel (II) complex Ni[P(OEt) 3 ](IMes Me )Br 2 is used as a catalyst to catalyze p-trimethylsilylstyrene and 2-phenylimidazo[1,2-a ] Hydroheteroarylation reaction of pyridine: Under the protection of argon, the catalyst (18 mg, 0.025 mmol, 5 mol%), sodium tert-butoxide (48 mg, 0.5 mmol), 2- Phenylimidazo[1,2-a]pyridine (97 mg, 0.5 mmol), p-trimethylsilylstyrene (154 ⁇ l, 0.75 mmol), toluene (1.5 ml) as solvent, at 100 o C for 18 hours, stop the reaction with water, extract the reaction product with ethyl acetate, and separate and purify it by column chromatography (using a mixed solvent of ethyl acetate/petroleum ether volume ratio of 1:2 as
  • Example 9 The divalent nickel (II) complex Ni[P(OEt) 3 ](IMes Me )Br 2 is used as a catalyst to catalyze 2,4,6-trimethylstyrene and 2-phenylimidazo[1, 2-a] Hydroheteroarylation of pyridine: under the protection of argon, add the catalyst (18 mg, 0.025 mmol, 5 mol%), sodium tert-butoxide (48 mg, 0.5 mmol) in sequence in the reaction flask , 2-phenylimidazo[1,2-a]pyridine (97 mg, 0.5 mmol), 2,4,6-trimethylstyrene (121 ⁇ l, 0.75 mmol), toluene (1.5 mL) As a solvent, react at 110 o C for 18 hours, terminate the reaction with water, extract the reaction product with ethyl acetate, and separate and purify it by column chromatography (using a mixed solvent of ethyl acetate/petrole
  • Example 11 Divalent nickel (II) complex Ni[P(OEt) 3 ](IMes Me )Br 2 is used as a catalyst to catalyze 1-vinylnaphthalene and 2-phenylimidazo[1,2-a]pyridine Hydrogen heteroarylation reaction: under the protection of argon, the catalyst (18 mg, 0.025 mmol, 5 mol%), sodium tert-butoxide (48 mg, 0.5 mmol), 2-phenyl Imidazo[1,2-a]pyridine (97 mg, 0.5 mmol), 1-vinylnaphthalene (111 ⁇ l, 0.75 mmol), toluene (1.5 ml) were used as solvents, and reacted at 110 o C for 18 hours , the reaction was terminated with water, the reaction product was extracted with ethyl acetate, separated and purified by column chromatography (using a mixed solvent of ethyl acetate/petroleum ether volume ratio of 1:2 as the developing solvent),
  • Example 12 Divalent nickel (II) complex Ni[P(OEt) 3 ](IMes Me )Br 2 is a catalyst, catalyzing 4-vinylbiphenyl and 2-phenylimidazo[1,2-a] Hydroheteroarylation reaction of pyridine: Under argon protection, add catalyst (18 mg, 0.025 mmol, 5 mol%), sodium tert-butoxide (48 mg, 0.5 mmol), 2-benzene Imidazo[1,2-a]pyridine (97mg, 0.5mmol), 4-vinylbiphenyl (135mg, 0.75mmol), toluene (1.5ml) were used as solvents, and reacted at 110 o C for 16 Hours, the reaction was terminated with water, the reaction product was extracted with ethyl acetate, separated and purified by column chromatography (using a mixed solvent with a volume ratio of ethyl acetate/petroleum ether of 1:2 as the developing solvent), and
  • Example 13 Divalent nickel (II) complex Ni[P(OEt) 3 ](IMes Me )Br 2 is used as a catalyst to catalyze 2-vinylthiophene and 2-phenylimidazo[1,2-a]pyridine Hydrogen heteroarylation reaction: under the protection of argon, the catalyst (18 mg, 0.025 mmol, 5 mol%), sodium tert-butoxide (48 mg, 0.5 mmol), 2-phenyl Imidazo[1,2-a]pyridine (97 mg, 0.5 mmol), 2-vinylthiophene (79 ⁇ l, 0.75 mmol), toluene (1.5 ml) were used as solvents, and reacted at 120 o C for 15 hours , the reaction was terminated with water, the reaction product was extracted with ethyl acetate, and separated and purified by column chromatography (using a mixed solvent with a volume ratio of ethyl acetate/petroleum ether of 1:2 as the developing
  • Example 14 Divalent nickel (II) complex Ni[P(OEt) 3 ](IMes Me )Br 2 is a catalyst, catalyzing 2-vinyl-N-methylpyrrole and 2-phenylimidazo[1, 2-a] Hydroheteroarylation of pyridine: under the protection of argon, add the catalyst (18 mg, 0.025 mmol, 5 mol%), sodium tert-butoxide (48 mg, 0.5 mmol) in sequence in the reaction flask , 2-phenylimidazo[1,2-a]pyridine (97 mg, 0.5 mmol), 2-vinyl-N-methylpyrrole (90 ⁇ l, 0.75 mmol), toluene (1.5 ml) Solvent, react at 100 o C for 15 hours, stop the reaction with water, extract the reaction product with ethyl acetate, and separate and purify it by column chromatography (the mixed solvent of ethyl acetate/petroleum ether with a volume
  • Example 15 Divalent nickel (II) complex Ni[P(OEt) 3 ](IMes Me )Br 2 is a catalyst, catalyzing styrene and 2-(4-methoxyphenyl) imidazo[1,2 -a] Heteroarylation reaction of pyridine: Under argon protection, Ni[P(OEt)3](IMesMe)Br2 catalyst (18 mg, 0.025 mmol, 5 mol%), t- Sodium butoxide (48 mg, 0.5 mmol), 2-(4-methoxyphenyl)imidazo[1,2-a]pyridine (112 mg, 0.5 mmol), styrene (86 ⁇ l, 0.75 mmol), toluene (1.5 ml) as solvent, reacted at 120°C for 18 hours, terminated the reaction with water, extracted the reaction product with ethyl acetate, separated and purified by column chromatography (the volume ratio of ethyl acetate
  • Embodiment 16 Divalent nickel (II) complex Ni[P(OEt) 3 ](IMes Me )Br 2 is a catalyst, catalyzes styrene and 2-(4-trifluoromethylphenyl) imidazo[1, 2-a] Heteroarylation reaction of pyridine: Under argon protection, Ni[P(OEt)3](IMesMe)Br2 catalyst (18 mg, 0.025 mmol, 5 mol%), Sodium tert-butoxide (48 mg, 0.5 mmol), 2-(4-trifluoromethylphenyl)imidazo[1,2-a]pyridine (131 mg, 0.5 mmol), styrene (86 ⁇ l , 0.75 mmol), toluene (1.5 ml) as solvent, reacted at 110°C for 15 hours, terminated the reaction with water, extracted the reaction product with ethyl acetate, separated and purified by column chromatography (according to the

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  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

La présente invention concerne un procédé de synthèse d'un composé de 2-phényl-5-benzyl-imidazo[1,2-a]pyridine. L'utilisation d'un complexe de nickel (II) composé ayant la formule moléculaire de Ni[P(OEt)3]{[RNC(CH3)C(CH3)NR]C}Br2 (R étant 2,4,6-triméthylphényle) en tant que catalyseur, permet de synthétiser le composé de 2-phényl-5-benzyl-imidazo[1,2-a]pyridine au moyen d'une réaction d'hétéroarylation d'hydrogène d'un composé aryle éthylène et d'un composé 2-phénylimidazo[1,2-a]pyridine en présence de tert-butoxyde de sodium. La présente invention concerne une nouvelle réaction d'hétéroarylation d'hydrogène basée sur un catalyseur de nickel, et concerne un nouveau procédé de synthèse du composé de 2-phényl-5-benzyl-imidazo[1,2-a]pyridine, qui est un premier cas de préparation du composé de 2-phényl-5-benzyl-imidazo[1,2-a]pyridine obtenu à l'aide d'un catalyseur de nickel au moyen d'une réaction d'hétéroarylation d'hydrogène du composé d'aryle éthylène et du composé de 2-phénylimidazo[1,2-a]pyridine.
PCT/CN2022/075264 2022-01-30 2022-01-30 Procédé de synthèse d'un composé 2-phényl-5-benzyl-imidazo[1,2-a]pyridine WO2023142128A1 (fr)

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