Category: 25637-16-5

Synthetic Route of C5H9BrOIn 2019 ,《Discovery of novel, potent, isosteviol-based antithrombotic agents》 appeared in European Journal of Medicinal Chemistry. The author of the article were Chen, Peng; Zhang, Dianwen; Li, Meng; Wu, Qiong; Lam, Yuko P. Y.; Guo, Yan; Chen, Chen; Bai, Nan; Malhotra, Shipra; Li, Wei; O’Connor, Peter B.; Fu, Hongzheng. The article conveys some information:

Thrombosis is a pathol. coagulation process and can lead to many serious thrombotic diseases. Here, we report a novel potent antithrombotic compound (6k) based on isosteviol with anticoagulant and antiplatelet activities. 6k selectively inhibited FXa (Ki = 0.015μM) against a panel of serine proteases and showed excellent anticoagulant activity (significant prolongation of ex vivo PT and aPTT over the vehicle, p < 0.01). 6k also significantly inhibited ADP-induced platelet aggregation in rats relative to the vehicle (p < 0.01). Furthermore, 6k exhibited potent ex vivo and in vivo antithrombotic activity in rats relative to the vehicle (p < 0.01 and p < 0.0001, resp.). Novel structure 6k, with potent antithrombotic activity, is expected to lead a promising approach for the development of antithrombotic agents. The experimental part of the paper was very detailed, including the reaction process of 4-Bromotetrahydropyran(cas: 25637-16-5Synthetic Route of C5H9BrO)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Synthetic Route of C5H9BrO

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Nirogi, Ramakrishna; Mohammed, Abdul Rasheed; Shinde, Anil Karbhari; Gagginapally, Shankar Reddy; Kancharla, Durga Malleshwari; Ravella, Srinivasa Rao; Bogaraju, Narsimha; Middekadi, Vanaja Reddy; Subramanian, Ramkumar; Palacharla, Raghava Choudary; Benade, Vijay; Muddana, Nageswararao; Abraham, Renny; Medapati, Rajesh Babu; Thentu, Jagadeesh Babu; Mekala, Venkat Reddy; Petlu, Surendra; Lingavarapu, Bujji Babu; Yarra, Sivasekhar; Kagita, Narendra; Goyal, Vinod Kumar; Pandey, Santosh Kumar; Jasti, Venkat published their research in Journal of Medicinal Chemistry in 2021. The article was titled 《Discovery and Preclinical Characterization of Usmarapride (SUVN-D4010): A Potent, Selective 5-HT4 Receptor Partial Agonist for the Treatment of Cognitive Deficits Associated with Alzheimer’s Disease》.SDS of cas: 25637-16-5 The article contains the following contents:

A series of oxadiazole derivatives were synthesized and evaluated as 5-hydroxytryptamine-4 receptor (5-HT4R) partial agonists for the treatment of cognitive deficits associated with Alzheimer’s disease. Starting from a reported 5-HT4R antagonist, a systematic structure-activity relationship was conducted, which led to the discovery of potent and selective 5-HT4R partial agonist 1-isopropyl-3-{5-[1-(3-methoxypropyl) piperidin-4-yl]-[1,3,4]oxadiazol-2-yl}-1H-indazole oxalate (Usmarapride, 12l)(I). It showed balanced physicochem.-pharmacokinetic properties with robust nonclin. efficacy in cognition models. It also showed disease-modifying potential, as it increased neuroprotective soluble amyloid precursor protein alpha levels, and dose-dependent target engagement and correlation of efficacy with oral exposures. Phase 1 clin. studies have been completed and projected efficacious concentration was achieved without any major safety concerns. Phase 2 enabling long-term safety studies have been completed with no concerns for further development. In the experiment, the researchers used 4-Bromotetrahydropyran(cas: 25637-16-5SDS of cas: 25637-16-5)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.SDS of cas: 25637-16-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

《Visible-Light-Driven Reductive Carboarylation of Styrenes with CO2 and Aryl Halides》 was written by Wang, Hao; Gao, Yuzhen; Zhou, Chunlin; Li, Gang. Application In Synthesis of 4-Bromotetrahydropyran And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

The first example of visible-light-driven reductive carboarylation of styrenes with CO2 and aryl halides in a regioselective manner has been achieved. A broad range of aryl iodides and bromides were compatible with this reaction. Moreover, pyridyl halides, alkyl halides, and even aryl chlorides were also viable with this method. These findings may stimulate the exploration of novel visible-light-driven Meerwein arylation-addition reactions with user-friendly aryl halides as the radical sources and the photocatalytic utilization of CO2. Thus, e.g., reaction of 1,1-diphenylethylene with PhI and CO2 under blue light in presence of [Ir(ppy)2(dtbbpy)]PF6 photocatalyst and hydrogen atom transfer catalyst DABCO with HCO2K as terminal reductant and K2CO3 as base in DMSO followed by methylation afforded I (82%, 78% isolated). In the experiment, the researchers used 4-Bromotetrahydropyran(cas: 25637-16-5Application In Synthesis of 4-Bromotetrahydropyran)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Application In Synthesis of 4-Bromotetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Reference of 4-BromotetrahydropyranIn 2021 ,《Nickel-Catalyzed Ipso/Ortho Difunctionalization of Aryl Bromides with Alkynes and Alkyl Bromides via a Vinyl-to-Aryl 1,4-Hydride Shift》 appeared in Journal of the American Chemical Society. The author of the article were He, Yuli; Borjesson, Marino; Song, Huayue; Xue, Yuhang; Zeng, Daning; Martin, Ruben; Zhu, Shaolin. The article conveys some information:

Polysubstituted arenes are ubiquitous structures in a myriad of medicinal agents and complex mols. Herein, a new catalytic blueprint that merges the modularity of nickel catalysis for bond formation with the ability to enable a rather elusive 1,4-hydride shift at arene sp2 C-H sites, thus allowing access to ipso/ortho-difunctionalized arenes from readily available aryl halides under mild conditions and exquisite selectivity profile is reported. The experimental part of the paper was very detailed, including the reaction process of 4-Bromotetrahydropyran(cas: 25637-16-5Reference of 4-Bromotetrahydropyran)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Reference of 4-Bromotetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Borlinghaus, Niginia; Schoenfeld, Barbara; Heitz, Stephanie; Klee, Johanna; Vukelic, Stella; Braje, Wilfried M.; Jolit, Anais published an article in 2021. The article was titled 《Enabling Metallophotoredox Catalysis in Parallel Solution-Phase Synthesis Using Disintegrating Reagent Tablets》, and you may find the article in Journal of Organic Chemistry.Recommanded Product: 4-Bromotetrahydropyran The information in the text is summarized as follows:

Compressed tablets containing a mixture of a photocatalyst, a nickel catalyst, an inorganic base, and an inert excipient are employed as a fast, safe, and user-friendly chem. delivery system for two different metallophotoredox-catalyzed reactions. This delivery method simplifies the preparation of compound libraries using photoredox chem. in a parallel setting. The reagent tablets were successfully applied to late-stage functionalization of drug-like intermediates. These tablets can be prepared with various reagents and catalysts in different sizes and be stored on the bench thanks to blister packaging. The experimental process involved the reaction of 4-Bromotetrahydropyran(cas: 25637-16-5Recommanded Product: 4-Bromotetrahydropyran)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Recommanded Product: 4-Bromotetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Garbacz, Mateusz; Stecko, Sebastian published their research in Organic & Biomolecular Chemistry in 2021. The article was titled 《Synthesis of chiral branched allylamines through dual photoredox/nickel catalysis》.Application of 25637-16-5 The article contains the following contents:

This work describes a new approach for the preparation of allylamines, e.g., (S,E)-Et 7-((tert-butoxycarbonyl)amino)oct-5-enoate via cross-coupling of alkyl bromides, e.g., Et 4-bromobutanoate with simple 3-bromoallylamines, e.g., N-Boc (S,E)-4-bromobut-3-en-2-amine by merging the photoredox approach and Ni catalysis. The reaction proceeds under mild conditions, under blue light irradiation, and in the presence of an organic dye, 4CzIPN, as a photocatalyst. The scope of suitable reaction partners is broad, including alkyl bromides bearing reactive functionalities (e.g., esters, nitriles, aldehydes, ketones, epoxides) and N-protected allylamines, as well as N-allylated secondary and tertiary amines and heterocycles. The employment of non-racemic starting materials allows for rapid and easy construction of complex multifunctional allylamine derivatives without the loss of enantiomeric purity. The results came from multiple reactions, including the reaction of 4-Bromotetrahydropyran(cas: 25637-16-5Application of 25637-16-5)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Application of 25637-16-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

In 2019,Journal of Organic Chemistry included an article by Castroagudin, Marina; Lobato, Ruben; Martinez-Garcia, Lucas; Sardina, F. Javier; Paleo, M. Rita. Application of 25637-16-5. The article was titled 《Bis-enolates with extended π-conjugation are powerful nucleophiles. Study of their alkylation reactions with very hindered C-electrophiles》. The information in the text is summarized as follows:

Bis-enolates with extended π-conjugation, prepared by alkali metal mediated reduction of several aromatic and unsaturated diesters, can be efficiently and regioselectively alkylated with very hindered C-electrophiles, such as neopentyl, secondary and tertiary alkyl halides and tosylates. A one-step synthesis of 4-alkyl phthalates was derived from the reductive-alkylation of a phthalate diester with hindered halides followed by rearomatization with oxygen. Addnl., synthetic protocols have been developed to efficiently prepare complex fused- or spiro-bicycles from diisopropyl phthalate in just one or two steps. The experimental process involved the reaction of 4-Bromotetrahydropyran(cas: 25637-16-5Application of 25637-16-5)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.Application of 25637-16-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

SDS of cas: 25637-16-5In 2020 ,《A general carbonyl alkylative amination for tertiary amine synthesis》 was published in Nature (London, United Kingdom). The article was written by Kumar, Roopender; Floden, Nils J.; Whitehurst, William G.; Gaunt, Matthew J.. The article contains the following contents:

The ubiquity of tertiary alkylamines in pharmaceutical and agrochem. agents, natural products and small-mol. biol. probes has stimulated efforts towards their streamlined synthesis. Arguably the most robust method for the synthesis of tertiary alkylamines is carbonyl reductive amination, which comprises two elementary steps: the condensation of a secondary alkylamine with an aliphatic aldehyde to form an all-alkyl-iminium ion, which is subsequently reduced by a hydride reagent. Direct strategies were sought for a ‘higher order’ variant of this reaction via the coupling of an alkyl fragment with an alkyl-iminium ion that was generated in situ. However, despite extensive efforts, the successful realization of a ‘carbonyl alkylative amination’ has not yet been achieved. Here the authors present a practical and general synthesis of tertiary alkylamines through the addition of alkyl radicals to all-alkyl-iminium ions. The process is facilitated by visible light and a silane reducing agent, which trigger a distinct radical initiation step to establish a chain process. This operationally straightforward, metal-free and modular transformation forms tertiary amines, without structural constraint, via the coupling of aldehydes and secondary amines with alkyl halides. The structural and functional diversity of these readily available precursors provides a versatile and flexible strategy for the streamlined synthesis of complex tertiary amines. In addition to this study using 4-Bromotetrahydropyran, there are many other studies that have used 4-Bromotetrahydropyran(cas: 25637-16-5SDS of cas: 25637-16-5) was used in this study.

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.SDS of cas: 25637-16-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Computed Properties of C5H9BrOIn 2021 ,《Design, synthesis and biological evaluations of a series of Pyrido[1,2-a]pyrimidinone derivatives as novel selective FGFR inhibitors》 appeared in European Journal of Medicinal Chemistry. The author of the article were Ran, Kai; Zeng, Jun; Wan, Guoquan; He, Xiaojie; Feng, Zhanzhan; Xiang, Wang; Wei, Wei; Hu, Xiang; Wang, Ningyu; Liu, Zhihao; Yu, Luoting. The article conveys some information:

Herein, the design and synthesis of pyrido[1,2-a]pyrimidinone derivatives I (R1 = methoxyethoxy, tert-butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl, 1H-pyrazol-4-yl, etc.) and II (R2 = Me, azetidin-3-yl, etc.; R3 = 3-[(propan-2-yl)amino]propyl, prop-2-yn-1-yl, cyclopropylmethyl, etc.) as potent FGFR inhibitors were described. Examination of structure-activity relationships and preliminary assessment identified I (R1 = 1-methyl-1H-pyrazol-4-yl) as a novel FGFR inhibitor that displayed excellent potency in vitro. Candidate I [R1 = 1-methyl-1H-pyrazol-4-yl (III)] suppressed the phosphorylation of FGFR signaling pathways and induced cell cycle arrest and apoptosis at low nanomolar concentration In the kinase inhibition profile, III showed excellent kinase selectivity for the FGFR family. Furthermore, III showed higher aqueous solubility than Erdafitinib. Moreover, III exhibited potent antitumor activity (tumor growth inhibition = 106.4%) in FGFR2-amplified SNU-16 gastric cancer xenograft model using a daily oral dose of 30 mg/kg. These results suggest that III is a promising candidate for further drug development. In the experimental materials used by the author, we found 4-Bromotetrahydropyran(cas: 25637-16-5Computed Properties of C5H9BrO)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.Computed Properties of C5H9BrO

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Liu, Yi; Zhou, Cuihan; Jiang, Meijing; Arndtsen, Bruce A. published an article in 2022. The article was titled 《Versatile Palladium-Catalyzed Approach to Acyl Fluorides and Carbonylations by Combining Visible Light- and Ligand-Driven Operations》, and you may find the article in Journal of the American Chemical Society.Reference of 4-Bromotetrahydropyran The information in the text is summarized as follows:

The development of a general palladium-catalyzed carbonylative method to synthesize acyl fluorides RC(O)F (R = n-Bu, cyclohexyl, 4-methylphenyl, pyridin-3-yl, etc.) from aryl, heteroaryl, alkyl, and functionalized organic halides RX was described. Mechanistic anal. suggests that the reaction proceeds via the unique, synergistic combination of visible light photoexcitation of Pd(0) to induce oxidative addition with a ligand-favored reductive elimination. These together create a unidirectional catalytic cycle that is uninhibited by the classical effect of carbon monoxide coordination. Coupling the catalytic formation of acyl fluorides with their subsequent nucleophilic reactions has opened a method to perform carbonylation reactions with unprecedented breadth, including the assembly of highly functionalized carbonyl-containing products.4-Bromotetrahydropyran(cas: 25637-16-5Reference of 4-Bromotetrahydropyran) was used in this study.

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.Reference of 4-Bromotetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics