Selective Phenol Alkylation: An Improved Preparation of Efaproxiral

Anderson, Joanne E.; Davis, Roman; Fitzgerald, Russ N.; Haberman, Jannine M.

doi:10.1080/00397910600636527

Cited by 31 publications

(17 citation statements)

References 4 publications

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“…Boronic acid‐catalyzed (BAC) amidation has also been documented . The catalytic methodology is applied in the synthesis of efaproxiral, a drug used for the treatment of cancer, by GlaxoSmithKline (Scheme ) . Limitations of these catalytic methods are the high catalyst loading, inability to recycle the catalyst, limited substrate scope, and prolonged reaction time.…”

Section: Transformations In Green Solventsmentioning

confidence: 99%

A Glimpse into Green Chemistry Practices in the Pharmaceutical Industry

et al. 2020

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Scheme2.Heck-Mizorokir eaction in g-valerolactone.Scheme3.Synthesis of 1-butyl-3-methylimidazoliumchloride using scCO 2 .Scheme1.Suzuki-Miyaura coupling in 2-Me-THF.Scheme4.Improved synthetic route to sildenafilc itrate.Scheme5.Improved synthetic route to ibuprofen.Scheme6.Cu-catalyzed cyclopropanation.Scheme17. Amination in synthesis of efaproxiral.Scheme15. Peptide couplingsint he synthesis of sildenafil and sunitinib.Scheme16. Amide couplings in water.Scheme20. Couplings of unactivated (iso)quinolines in PS-750-M.Scheme21. PS-750-M as ar eplacement for toxic polar-aprotic solvent for sp 2 -sp 3 couplings.Scheme22. Recyclable palladium nanoparticles in PS-750-M for olefins ynthesis through carbene insertion.Scheme23. Drugmolecules containingC ÀNb onds.Scheme24. Recyclable bimetallic nanoparticles for sustainable Buchwald-Hartwig aminations in water.Scheme25. Ac omparison between chemistryinw ater versus chemistryino rganic solvents (Novartis Pharmaceuticals).

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Section: Transformations In Green Solventsmentioning

confidence: 99%

A Glimpse into Green Chemistry Practices in the Pharmaceutical Industry

et al. 2020

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“…For solving these problems, new methods have been replaced with them such as metal‐free methods (like organo‐catalysts) and boron reagents. Nevertheless, it faces with low atomic efficiency and difficult products separation . Amide synthesis methods catalyzed with metals have been drawn attention.…”

Section: Introductionmentioning

confidence: 99%

Oxidative amidation of benzyl alcohol, benzaldhyde, benzoic acid styrene and phenyl acetylene catalyzed by ordered mesoporous HKUST‐1‐Cu: Effect of surface area on oxidative amidation reaction

Mohebali

Mahjoub

Karimi

et al. 2019

Applied Organom Chemis

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HKUST‐1‐Cu synthesized in the presence and absence of P‐123 trough solvotermal method. After characterization using some different microscopic and spectroscopic techniques such as XRD, FT‐IR, SEM, ICP, BET and TEM its catalytic activity was investigated in the oxidative coupling of benzyl alcohol, benzaldhyde, benzoic acid, styrene and phenyl acetylene with N,N‐dialkylformamides for the preparation of N,N‐dimethylformamides. Different derivatives of tertiary amides were synthesized in moderate to good yields in the presence of just ~0.28 mol% of this catalytic system. Reusability of the synthesized catalysts was examined and catalysts were reusable for 8 times without significant decrease in optimized conditions.

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“…Amide is an essential functional group for drug development with an increasing demand in the pharmaceutical industry. It is a useful compound for the synthesis of efaproxiral intermediate, which is manufactured for metastatic cancer therapy . Typically, it is synthesized by the reactions of carboxylic acids with amines (using coupling agents) or through the direct catalytic amidation of aldehydes and amines with a catalyst.…”

Section: Homogeneous/heterogeneous Catalysismentioning

confidence: 99%

Catalysis at room temperature: perspectives for future green chemical processes

Lam

Chau

et al. 2014

WIREs Energy & Environment

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Catalytic processes have been one of the main pillars of the chemical industry in recent years. Protocols that make use of homogeneous and heterogeneous catalysts have been extensively implemented for the production of fine chemicals, fuels, materials, and relevant products. Importantly, the need for benign by design processes and technologies became recently a major driver in both research and industry for a more sustainable future. This contribution has been aimed to discuss and highlight key examples on room temperature catalytic processes as one of the most relevant research avenues for future developments in catalysis.

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Selective Phenol Alkylation: An Improved Preparation of Efaproxiral

Cited by 31 publications

References 4 publications

A Glimpse into Green Chemistry Practices in the Pharmaceutical Industry

A Glimpse into Green Chemistry Practices in the Pharmaceutical Industry

Oxidative amidation of benzyl alcohol, benzaldhyde, benzoic acid styrene and phenyl acetylene catalyzed by ordered mesoporous HKUST‐1‐Cu: Effect of surface area on oxidative amidation reaction

Catalysis at room temperature: perspectives for future green chemical processes

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