- Preparation method of benzbromarone
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The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of benzbromarone. According to the method disclosed by the invention, polystyrene-loaded aluminum trichloride is used as a catalyst to carry out Friedel-Crafts acylation reaction, so that the catalytic effect is good, and the catalyst can be recycled, in the demethylation reaction process, aluminum trichloride is adopted to replace common pyridine hydrochloride, so that the reaction temperature can be reduced, and the yield can be increased, in the bromination reaction, sodium sulfide and hydrogen peroxide are adopted to replace bromine, so that the technical problems of strong corrosivity of bromine, great harm to human bodies and environmental pollution are solved, and meanwhile, the yield can be further improved.
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- Synthesis method of benzbromarone key intermediate
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The invention relates to the technical field of biological medicines, in particular to a synthesis method of a benzbromarone key intermediate, which comprises the following steps: carrying out Friedel-Crafts acylation reaction on 2-ethyl benzofuran and p-methoxybenzoyl chloride under the catalysis of aluminum trichloride by taking methylbenzene as a solvent to generate 2-ethyl-3-p-methoxybenzoyl-benzofuran; and carrying out a demethylation reaction on 2-ethyl-3-p-methoxybenzoyl-benzofuran and aluminum trichloride by taking toluene as a solvent to obtain the key intermediate 2-ethyl-3-p-hydroxybenzoyl-benzofuran of benzbromarone. The synthesis method of the benzbromarone key intermediate, provided by the invention, is mild in reaction condition, the obtained product is relatively high in purity and yield, and the synthesis method has a good industrial production prospect.
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Paragraph 0010; 0027; 0030-0032; 0035-0036
(2021/07/28)
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- Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds
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2,3-Disubstituted benzofurans were synthesized from acrolein dimer and 1,3-dicarbonyl compounds by using N-bromosuccinimide as an oxidizing agent. The method was used to synthesize two commercial drug molecules, benzbromarone and amiodarone. The proposed mechanism of the reaction involves a N-bromosuccinimide (NBS)-assisted autotandem catalysis with Lewis acid catalyst. To proof the proposed mechanism, an intermediate was isolated successfully, which can be converted to 4,5,6,7-tetrahydrobenzofurans.
- Huang, Wenbo,Xu, Jing,Liu, Changhui,Chen, Zhiyan,Gu, Yanlong
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p. 2941 - 2950
(2019/02/26)
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- Preparation method of 2-ethyl-3-(4-hydroxylbenzoyl) benzofuran
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The invention discloses a preparation method of 2-ethyl-3-(4-hydroxylbenzoyl) benzofuran. According to the preparation method, at first, 1-(4-methoxyphenyl)-1,3-pentanedione and acrolein dimer are taken as raw materials to carry out reactions in the presence of an acid catalyst and a halogenation reagent to prepare 2-ethyl-3-(4-methoxyphenyl) benzofuran; then 2-ethyl-3-(4-methoxyphenyl) benzofuranis processed in an organic solvent containing an acid catalyst, and after de-methylation reactions, 2-ethyl-3-(4-hydroxylbenzoyl) benzofuran is obtained. The whole process of key preparation technologies and parameters of each reaction step are optimized; and compared with a conventional synthesis method, the provided preparation method has the advantages of good economy, high selectivity, littleenvironmental pollution, and large industrial application value.
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Paragraph 0030; 0036; 0039; 0042-0044; 0048
(2018/11/04)
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- Industrial production method of benzarone
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The invention relates to an industrial production method of benzarone. The method comprises the following steps: (1) 2-ethylbenzofuran, 4-methoxybenzoyl chloride and an inert solvent are added to a reactor and subjected to a reaction at 15-30 DEG C for 0.5-1 h, Lewis acid is added in batches, a thermal insulated reaction is performed for 3-4 h, then quenching, acidification, water washing, distillation, crystallization and filtering are performed, and a benzarone intermediate is obtained; (2) the benzarone intermediate, Lewis acid and the inert solvent are added to another reactor and subjected to a reaction at 15-30 DEG C for 0.5-1 h, the temperature is increased to 100 DEG C or lower, a thermal insulated reaction is performed for 2-3 h, the same postprocessing is performed, and benzaroneis obtained. Friedel-Crafts acylation is adopted, reaction conditions are relatively mild, high temperature and high energy consumption are avoided, so that the problems of high temperature and low yield in production in the prior art are solved, and the method has good application prospect.
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Paragraph 0016-0030
(2018/09/12)
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- Compound for treatment or prevention of hyperuricemia or gout
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The invention discloses a compound for treatment or prevention of hyperuricemia or gout. The compound is the compound shown as formula (I) or formula (II) or pharmaceutical acceptable salts thereof. The compound or its pharmaceutical acceptable salts can be applied to urate excretion promotion so as to treat or prevent hyperuricemia or gout. (formula (1), formula (II)).
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- Ligand-free, palladium-catalyzed dihydrogen generation from TMDS: Dehalogenation of aryl halides on water
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A mild and environmentally attractive dehalogenation of functionalized aryl halides has been developed using nanoparticles formed from PdCl2 in the presence of tetramethyldisiloxane (TMDS) on water. The active catalyst and reaction medium can be recycled. This method can also be applied to cascade reactions in a one-pot sequence.
- Bhattacharjya, Anish,Klumphu, Piyatida,Lipshutz, Bruce H.
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supporting information
p. 1122 - 1125
(2015/03/14)
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- DEVELOPING POTENT URATE TRANSPORTER INHIBITORS: COMPOUNDS DESIGNED FOR THEIR URICOSURIC ACTION
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A compound represented by the general Formula (I): a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a pro-drug thereof, a deuterated radio-labeled analog thereof, and mixtures of any of the foregoing, wherein: A - K are individually selected from carbon or nitrogen; X = -O, -NR1,or -S; R1-11 are individually selected from the group consisting of-H, C1-C6 alkyl, C6-C aryl, substituted C6-C14 aryl, C1-C14-alkoxy, halogen, hydroxyl, carboxy, cyano, C1-C6-alkanoyloxy, C1-C6-alkylthio, C1-C6-alkylsulfonyl, trifluoromethyl, hydroxy, C2-C6-alkoxycarbonyl, C2-C6-alkanoylamino, -O-R12, S-R12,-SO2-Ri2, -NHSO2R12 and -NHCO2R12, wherein R12 is phenyl, naphthyl, or phenyl or naphthly substituted with one to three groups selected from C1-C6-alkyl, C6-C10 aryl,C1-C6-alkoxy and halogen, and C4-C20 hydroxyheteroaryl wherein the heteroatoms are selected from the group consisting of sulfur, nitrogen, and oxygen.
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- Developing potent human uric acid transporter 1 (hURAT1) inhibitors
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The kidneys are a vital organ in the human body. They serve several purposes including homeostatic functions such as regulating extracellular fluid volume and maintaining acid-base and electrolyte balance and are essential regarding the excretion of metabolic waste. Furthermore, the kidneys play an important role in uric acid secretion/reabsorption. Abnormalities associated with kidney transporters have been associated with various diseases, such as gout. The current study utilized Xenopus oocytes expressing human uric acid transporter 1 (hURAT1; SLC22A12) as an in vitro method to investigate novel compounds and their ability to inhibit 14C-uric acid uptake via hURAT1. We have prepared and tested a series of 2-ethyl-benzofuran compounds and probed the hURAT1 in vitro inhibitor structure-activity relationship. As compared to dimethoxy analogues, monophenols formed on the C ring showed the best in vitro inhibitory potential. Compounds with submicromolar (i.e., IC 50 1000 nM) inhibitors were prepared by brominating the corresponding phenols to produce compounds with potent uricosuric activity.
- Wempe, Michael F.,Jutabha, Promsuk,Quade, Bettina,Iwen, Timothy J.,Frick, Morin M.,Ross, Ian R.,Rice, Peter J.,Anzai, Naohiko,Endou, Hitoshi
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p. 2701 - 2713
(2011/06/25)
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- Preparation of 2-alkyl-3-(4-hydroxybenzoyl)benzofuran
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The invention relates to new molecular complexes of general formula: STR1 in which R represents a straight- or branched-chain alkyl radical having from 1 to 4 carbon atoms and R1 represents one of the radicals: STR2 These molecular complexes are especially useful for the preparation of 2-alkyl-3-(4-hydroxybenzoyl)benzofurans.
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