759-67-1Relevant articles and documents
A Pd-Catalyzed [4 + 2] Annulation Approach to Fluorinated N-Heterocycles
García-Vázquez, Víctor,Hoteite, Larry,Lakeland, Christopher P.,Watson, David W.,Harrity, Joseph P. A.
supporting information, p. 2811 - 2815 (2021/05/05)
3-Fluoro- and trifluoromethylthio-piperidines represent important building blocks for discovery chemistry. We report a simple and efficient method to access analogs of these compounds that are armed with rich functionality allowing them to be chemoselectively derivatized with high diastereocontrol.
Method for continuously preparing voriconazole intermediate ethyl 2-fluoro-3-oxopentanoate
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Paragraph 0023-0037, (2020/04/02)
The invention discloses a method for continuously preparing a voriconazole intermediate, namely ethyl 2-fluoro-3-oxopentanoate. The method comprises the following steps: feeding a reaction solvent, ethyl 2-fluoro-acetate, propionyl chloride and sodium hydrogen into a reaction kettle for a reaction, then adding boric acid and acid anhydride, feeding a reaction liquid into a centrifugal machine, continuously feeding a supernatant into the middle part of a rectifying tower for heating and rectifying, condensing light components at the top of the tower, allowing the condensed light components to flow back to the reaction kettle, and collecting a heavy component product from the bottom of the tower so as to obtain the voriconazole intermediate. According to the invention, boric acid and acid anhydride are added after the reaction is finished, so a reaction byproduct, namely 2-fluoro-3-oxopentanoic acid is converted into 2-fluoro-3-oxopentanoic acid-O3,O4-borodiacetate which can be easily separated from a main product, so the purity of the product is further improved; low-energy-consumption, simple, rapid and continuous production is realized; and the yield of the obtained reaction product ethyl 2-fluoro-3-oxopentanoate is greater than 90%, and the purity of the product is 98% or above.
DIARYLTHIOHYDANTOIN COMPOUND AS ANDROGEN RECEPTOR ANTAGONIST
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Paragraph 0664-0666, (2020/07/07)
The present application belongs to the field of medicine. In particular, the present application relates to a diarylthiohydantoin compound as an androgen receptor antagonist or a pharmaceutically acceptable salt thereof, a preparation method of the same, a pharmaceutical composition comprising the compound, and a use thereof in treating a cell proliferative disease mediated by androgen. The compound of the present application has good antagonistic effect on androgen receptor and exhibits excellent antitumor effect.
A 4 - (1-bromo-ethyl) - 5-fluoro-6-chloro-pyrimidine synthesis method
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Paragraph 0023; 0033; 0034; 0035, (2017/02/23)
The invention discloses a method for synthesizing 4-(1-bromoethyl) -5-fluoro-6-chloropyrimidine. The synthesis method comprises the steps of reacting 2-fluoro-ethyl acetate which is inexpensive and readily available and is used as an initial material with propionyl chloride under basic conditions in a solvent to synthesize an intermediate product 2-fluoro propionyl ethyl acetate; then carrying out cyclization on 2-fluoro propionyl ethyl acetate and formamidine acetate as well as a base in a solvent to obtain a cyclized product; then chlorinating the cyclized product with a chlorinating reagent; and finally adding a brominating reagent and brominating the chlorinated product in the presence of an initiator to obtain 4-(1-bromoethyl) -5-fluoro-6-chloropyrimidine. The synthesis method disclosed by the invention has the advantages of simple process, available raw materials, high yield, safety and environmental protection, and is convenient to industrialize.
A facile synthesis of α-fluoro ketones catalyzed by [Cp*IrCl2]2
Ahlsten, Nanna,Bartoszewicz, Agnieszka,Agrawal, Santosh,Martin-Matute, Belen
supporting information; experimental part, p. 2600 - 2608 (2011/10/02)
Allylic alcohols are isomerized into enolates (enols) by [Cp*IrCl2]2. The enolates react with Selectfluor present in the reaction media. This method produces α-fluoro ketones as single constitutional isomers in high yields. Georg Thieme Verlag Stuttgart. New York.
Synthesis of highly functionalized biaryls by condensation of 2-fluoro-1,3-bis(silyloxy) 1,3-dienes with 3-cyanochromones and subsequent domino "retro-Michael/aldol/fragmentation"
Ibad, Muhammad Farooq,Abid, Obaid-Ur-Rahman,Adeel, Muhammad,Nawaz, Muhammad,Wolf, Verena,Villinger, Alexander,Langer, Peter
supporting information; experimental part, p. 8315 - 8318 (2011/02/28)
The Me3SiOTf-mediated condensation of 1-ethoxy-2-fluoro-1,3- bis(trimethylsilyloxy) 1,3-dienes with 3-cyanochromones afforded 3-cyano-2-(4-ethoxy-3-fluoro-2,4-dioxobutyl)chroman-4-ones. Their reaction with triethylamine afforded fluorinated azaxanthones or biaryls. The product distribution depends on the structure of the diene. The formation of the biaryls can be explained by an unprecedented domino "retro-Michael/aldol/ fragmentation" reaction.
Acylation of Fluorocarbethoxy-Substituted Ylids: A Simple and General Route to α-Fluoro β-Keto Esters
Thenappan, Alagappan,Burton, Donald J.
, p. 273 - 277 (2007/10/02)
(Fluorocarbethoxymethylene)tri-n-butylphosphorane (3) reacts with acid chlorides and anhydrides to form the corresponding carbon acylated phosphonium salt 4, and hydrolysis of 4 under mild basic conditions provides RCOCFHCOOEt (8) in moderate yields.The reaction is applicable to primary, secondary, tertiary, cyclic, aromatic, and ester-substituted acid chlorides.Acylation with ethyl chloroformate and ethyl chlorothioformate leads to the diesters CFH(COOEt)2 and EtSCOCFHCOOEt.Extension of this reaction sequence to perfluorinated and partially fluorinated acid chlorides did not proceed cleanly to give the expected phosphonium salts.However, the anion derived from (EtO)2P(O)CFHC(O)OEt reacts with RFCOCl to form the corresponding C-acylated phosphonates 10, and hydrolysis of 10 gives RFCOCFHCOOEt.
AN EXPEDIENT SYNTHESIS OF α-FLUORO-β-KETOESTERS
Thenappan, Alagappan,Burton, Donald J.
, p. 6113 - 6116 (2007/10/02)
Acylation of fluorocarboethoxymethylene tri-n-butylphosphorane (4) followed by hydrolysis under mild basic conditions provides the title compounds (6) in good yields.
