- Assembly of α-(Hetero)aryl Nitriles via Copper-Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides
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α-(Hetero)aryl nitriles are important structural motifs for pharmaceutical design. The known methods for direct synthesis of these compounds via coupling with (hetero)aryl halides suffer from narrow reaction scope. Herein, we report that the combination of copper salts and oxalic diamides enables the coupling of a variety of (hetero)aryl halides (Cl, Br) and ethyl cyanoacetate under mild conditions, affording α-(hetero)arylacetonitriles via one-pot decarboxylation. Additionally, the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α-alkyl-substituted ethyl cyanoacetates proceeds smoothly at 60 °C, leading to the formation of α-alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities and heteroaryls.
- Chen, Ying,Xu, Lanting,Jiang, Yongwen,Ma, Dawei
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supporting information
p. 7082 - 7086
(2021/02/26)
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- Application of novel dimethyl carbonate methylation catalyst in preparation α- methyl phenylacetic acid
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The invention relates to the field, of medicine synthesis, and concretely relates to a novel dimethyl carbonate methylation catalyst α - in preparation IV methylbenzene acetic acid. as starting material I for preparing a target product, methylbenzeneacetic acid, by a methylation, decarboxylation and hydrolysis reaction, under the action of a catalyst by using a catalyst as a representative low-cost catalyst, in the form of a quaternary amine salt, and a catalyst prepared by using the catalyst as a representative low-cost catalyst, such as potassium α - potassium bromide acetate, as a catalyst, and a catalyst used in the, hydrolysis reaction of the quaternary, amine salt. IV. 98%. The preparation method comprises the following steps: preparing a target product from the quaternary ammonium. salt solution.
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Paragraph 0062-0064
(2020/03/17)
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- Application of novel dimethyl carbonate methylation catalyst in preparation α- methyl phenylacetic acid
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The invention relates to the field, of medicine synthesis, and concretely relates to a novel dimethyl carbonate methylation catalyst α - in preparation IV methylbenzene acetic acid. as starting material I for preparing a target product, methylbenzeneacetic acid, by a methylation, decarboxylation and hydrolysis reaction, under the action of a catalyst by using a catalyst as a representative low-cost catalyst, in the form of a quaternary amine salt, and a catalyst prepared by using the catalyst as a representative low-cost catalyst, such as potassium α - potassium bromide acetate, as a catalyst, and a catalyst used in the, hydrolysis reaction of the quaternary, amine salt. IV. 98%. The preparation method comprises the following steps: preparing a target product from the quaternary ammonium. salt solution.
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Paragraph 0063-0065
(2020/03/17)
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- Ketoprofen intermediate as well as preparation method and application thereof
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The invention relates to the field, of medicine synthesis, in particular to a ketoprofen intermediate and a preparation method and application. thereof to prepare the ketoprofen, reaction formula by sequentially performing an oxidation reaction, substitution reaction, deamination, deamination and an acidic hydrolysis reaction after formation of the isoxazole compound, by a Diels,Alder reaction with a phenylacetic acid by. a Diels :Alder reaction of a phenylacetic acid. In-flight, X2 or. Ortho or para, R to nitro or amino group1 - COCONR4 R5 , COX1 , COOR2 Or - CNCNCNR2 , R3 , R4 , R5 , R6 The same or different is H or C. 1 - C6 Alkyl, X1 , X2 The same or different is F, Cl, Br or I.
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Paragraph 0190-0192
(2020/03/12)
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- Ketoprofen intermediate as well as preparation method and application thereof
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The invention relates to the field of medicine synthesis, in particular to a Ketoprofen intermediate as well as a preparation method and application thereof. Ketoprofen is prepared from p--nitrohalobenzene and o-nitrohalobenzene or a mixture of the p-nitrohalobenzene and the o-nitrohalobenzene as raw materials by first performing Diels-Alder reaction on the raw materials and phenylacetonitrile toobtain an isoxazole compound, and then sequentially carrying out oxidation reaction, substitution reaction, reduction reaction, deamination, ester removal and acid hydrolysis reaction to prepare the ketoprofen. The reaction formula is as shown in the specification, wherein X2 and a group as shown in the specification are located in ortho-position or para-position of a nitro group or an amino group, R1 is-CONR4R5,-COX1,-COOR2 or-CN, R2, R3, R4 and R5 are same or differently H or a C1-C6 alkyl group, and X1 and X2 are the same or different, and are F, Cl, Br Or I.
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- Continuous flow synthesis of diaryl ketones by coupling of aryl Grignard reagents with acyl chlorides under mild conditions in the ecofriendly solvent 2-methyltetrahydrofuran
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An efficient continuous flow sequential synthesis of diaryl ketones was achieved by coupling of aryl Grignard reagents with acyl chlorides in the bio-derived “green” solvent 2-methyltetrahydrofuran (2-MeTHF) under mild reaction conditions (ambient temperature, 1 hour), allowing a safe and on-demand generation of 2-(3-benzoylphenyl)propionitrile with a productivity of 3.16 g hour?1
- Zhang, Chuan-Tao,Zhu, Rui,Wang, Zheng,Ma, Bing,Zajac, Adrian,Smiglak, Marcin,Xia, Chun-Nian,Castle, Steven L.,Wang, Wen-Long
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p. 2199 - 2204
(2019/01/26)
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- Method of utilizing continuous flow microreactor to synthesize benzophenone derivative
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The invention belongs to the technical field of organic synthesis, and particularly relates to a method of utilizing a continuous flow microreactor to synthesize a benzophenone derivative. The methodincludes: using aryl Grignard reagent and acyl chloride as raw materials; at normal temperature, continuously synthesizing the benzophenone derivative in the microreactor; recycling a reaction solvent2-methyl tetrahydrofuran. Problems of environmental pollution and reaction operation safety caused by the fact that conventional Fridel-Crafts reaction is excessively dependent on reagents like aluminum trichloride, ferric trichloride and zinc dichloride are avoided, the defect that novel catalytic processes are expensive in catalytic reagent and harsh in operation condition is made up, and continuous synthesis of a medical intermediate ketoprofen nitrile is realized efficiently. The method has the advantages of high operation convenience, high reaction safety, high yield, high efficiency andreaction solvent reusability and is environment-friendly and efficient.
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Paragraph 0054-0057
(2018/09/11)
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- HETEROAROMATIC RING COMPOUNDS
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Heteroaromatic ring compounds or pharmaceutically acceptable salts thereof, which have excellent characteristics and have strong curative effects to immuno-imbalance and choronic inflammation. Representative is the compound of the formula:
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- Process for the alpha-monoalkylation of arylacetonitriles, arylacetoesters and arylacetic acids
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A process for the α-monoalkylation of arylacetonitriles, arylacetoesters and arylacetic acids with dialkyl carbonates in liquid phase, in the presence of bases at temperatures ranging from about 100° C. to about 270° C.
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- A process for the alpha-monoalkylation of arylacetonitriles, arylacetoesters and arylacetic acids
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A process for the α-monoalkylation of arylacetonitriles, arylacetoesters and arylacetic acids with dialkyl carbonates in liquid phase, in the presence of bases at temperatures ranging from about 100°C to about 270°C.
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