25637-16-5| Page 12 of 14 | Heterocyclic Building Blocks-Tetrahydropyran

Zhang, Xiaheng’s team published research in Journal of the American Chemical Society in 2017 | 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.COA of Formula: C5H9BrO

In 2017,Zhang, Xiaheng; MacMillan, David W. C. published 《Direct Aldehyde C-H Arylation and Alkylation via the Combination of Nickel, Hydrogen Atom Transfer, and Photoredox Catalysis》.Journal of the American Chemical Society published the findings.COA of Formula: C5H9BrO The information in the text is summarized as follows:

A mechanism that enables direct aldehyde C-H functionalization has been achieved via the synergistic merger of photoredox, nickel, and hydrogen atom transfer catalysis. This mild, operationally simple protocol transforms a wide variety of com. available aldehydes, along with aryl or alkyl bromides, into the corresponding ketones in excellent yield. This C-H abstraction coupling technol. has been successfully applied to the expedient synthesis of the medicinal agent haloperidol. In the experiment, the researchers used many compounds, for example, 4-Bromotetrahydropyran(cas: 25637-16-5COA of Formula: C5H9BrO)

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

Wang, Guang-Zu’s team published research in Journal of the American Chemical Society in 2017 | CAS: 25637-16-5

In 2017,Wang, Guang-Zu; Shang, Rui; Cheng, Wan-Min; Fu, Yao published 《Irradiation-Induced Heck Reaction of Unactivated Alkyl Halides at Room Temperature》.Journal of the American Chemical Society published the findings.SDS of cas: 25637-16-5 The information in the text is summarized as follows:

The palladium-catalyzed Mizoroki-Heck reaction is arguably one of the most significant carbon-carbon bond-construction reactions to be discovered in the last 50 years, with a tremendous number of applications in the production of chems. This Nobel-Prize-winning transformation has yet to overcome the obstacle of its general application in a range of alkyl electrophiles, especially tertiary alkyl halides that possess eliminable β-hydrogen atoms. Whereas most palladium-catalyzed cross-coupling reactions utilize the ground-state reactivity of palladium complexes under thermal conditions and generally apply a single ligand system, authors report that the palladium-catalyzed Heck reaction proceeds smoothly at room temperature with a variety of tertiary, secondary, and primary alkyl bromides upon irradiation with blue light-emitting diodes in the presence of a dual phosphine ligand system. Also rationalized that this unprecedented transformation is achieved by utilizing the photoexcited-state reactivity of the palladium complex to enhance oxidative addition and suppress undesired β-hydride elimination. 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.

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

Ben-Tal, Yael’s team published research in Journal of the American Chemical Society in 2022 | CAS: 25637-16-5

In 2022,Ben-Tal, Yael; Lloyd-Jones, Guy C. published an article in Journal of the American Chemical Society. The title of the article was 《Kinetics of a Ni/Ir-Photocatalyzed Coupling of ArBr with RBr: Intermediacy of ArNiII(L)Br and Rate/Selectivity Factors》.Electric Literature of C5H9BrO The author mentioned the following in the article:

The Ni/Ir-photocatalyzed coupling of an aryl bromide (ArBr) with an alkyl bromide (RBr) has been analyzed using in situ LED-19F NMR spectroscopy. Four components (light, [ArBr], [Ni], [Ir]) are found to control the rate of ArBr consumption, but not the product selectivity, while two components ([(TMS)3SiH], [RBr]) independently control the product selectivity, but not the rate. A major resting state of nickel has been identified as ArNiII(L)Br, and 13C-isotopic entrainment is used to show that the complex undergoes Ir-photocatalyzed conversion to products (Ar-R, Ar-H, Ar-solvent) in competition with the release of ArBr. A range of competing absorption and quenching effects lead to complex correlations between the Ir and Ni catalyst loadings and the reaction rate. Differences in the Ir/Ni Beer-Lambert absorption profiles allow the rate to be increased by the use of a shorter-wavelength light source without compromising the selectivity. A minimal kinetic model for the process allows simulation of the reaction and provides insights for optimization of these processes in the laboratory In the experiment, the researchers used many compounds, for example, 4-Bromotetrahydropyran(cas: 25637-16-5Electric Literature of C5H9BrO)

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

Zhou, Wen-Jun’s team published research in Angewandte Chemie, International Edition in 2017 | CAS: 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.Safety of 4-Bromotetrahydropyran

In 2017,Zhou, Wen-Jun; Cao, Guang-Mei; Shen, Guo; Zhu, Xing-Yong; Gui, Yong-Yuan; Ye, Jian-Heng; Sun, Liang; Liao, Li-Li; Li, Jing; Yu, Da-Gang published 《Visible-Light-Driven Palladium-Catalyzed Radical Alkylation of C-H Bonds with Unactivated Alkyl Bromides》.Angewandte Chemie, International Edition published the findings.Safety of 4-Bromotetrahydropyran The information in the text is summarized as follows:

Reported herein is a novel visible-light photoredox system with Pd(PPh3)4 as the sole catalyst for the realization of the first direct cross-coupling of C(sp3)-H bonds in N-aryl tetrahydroisoquinolines with unactivated alkyl bromides. Moreover, intra- and intermol. alkylations of heteroarenes were also developed under mild reaction conditions. A variety of tertiary, secondary and primary alkyl bromides undergo reaction to generate C(sp3)-C(sp3) and C(sp2)-C(sp3) bonds in moderate to excellent yields. These redox-neutral reactions feature broad substrate scope (>60 examples), good functional-group tolerance and facile generation of quaternary centers. Mechanistic studies indicate that the simple palladium complex acts as the visible-light photocatalyst and radicals are involved in the process. The experimental part of the paper was very detailed, including the reaction process of 4-Bromotetrahydropyran(cas: 25637-16-5Safety of 4-Bromotetrahydropyran)

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

Xue, Weichao’s team published research in Angewandte Chemie, International Edition in 2018 | CAS: 25637-16-5

Application In Synthesis of 4-BromotetrahydropyranIn 2018 ,《Bench-Stable Stock Solutions of Silicon Grignard Reagents: Application to Iron- and Cobalt-Catalyzed Radical C(sp3)-Si Cross-Coupling Reactions》 was published in Angewandte Chemie, International Edition. The article was written by Xue, Weichao; Shishido, Ryosuke; Oestreich, Martin. The article contains the following contents:

A robust method for the preparation of silicon-based magnesium reagents is reported. The MgBr2 used in the lithium-to-magnesium transmetalation step is generated in situ from 1,2-dibromoethane and elemental magnesium in hot THF. No precipitation of MgBr2 occurs in the heat, and transmetalation at elevated temperature leads to homogeneous stock solutions of the silicon Grignard reagents that are stable and storable in the fridge. This method avoids the preparation of silicon pronucleophiles such as Si-Si and Si-B reagents. The new Grignard reagents were applied to unprecedented iron- and cobalt-catalyzed cross-coupling reactions of unactivated alkyl bromides. The functional-group tolerance of these magnesium reagents is excellent. In the experiment, the researchers used many compounds, for example, 4-Bromotetrahydropyran(cas: 25637-16-5Application In Synthesis of 4-Bromotetrahydropyran)

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

Tota, Arianna’s team published research in Chemical Communications (Cambridge, United Kingdom) in 2017 | CAS: 25637-16-5

Category: tetrahydropyranIn 2017 ,《Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers》 was published in Chemical Communications (Cambridge, United Kingdom). The article was written by Tota, Arianna; Zenzola, Marina; Chawner, Stephen J.; John-Campbell, Sahra St; Carlucci, Claudia; Romanazzi, Giuseppe; Degennaro, Leonardo; Bull, James A.; Luisi, Renzo. The article contains the following contents:

Direct synthesis of NH-sulfoximines from sulfides were achieved through O and NH transfer in the same reaction, occurring with complete selectivity. The reaction was mediated by bisacetoxyiodobenzene under simple conditions and employs inexpensive N-sources. Preliminary studies indicated that NH-transfer was likely to be first, followed by oxidation, but the reaction proceedes successfully in either order. A wide range of functional groups and biol. relevant compounds were tolerated. The use of AcO15NH4 affords 15N-labeled compounds The experimental process involved the reaction of 4-Bromotetrahydropyran(cas: 25637-16-5Category: tetrahydropyran)

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

Brief introduction of 25637-16-5

The synthetic route of 25637-16-5 has been constantly updated, and we look forward to future research findings.

25637-16-5, 4-Bromotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The compound (64 mg, 0.2 mmol) obtained in step 217 1 was dissolved in 6 dichloromethane (2.0 mL), 8 triethylamine (82 muL, 0.60 mmol) and 111 di-tert-butyl dicarbonate (48 mg, 0.22 mmol) were added, and the mixture was stirred at room temperature for two nights. To the reaction mixture was added 72 water, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated brine, and dried over sodium sulfate. The desiccant was filtered off, and the solvent was evaporated. To a residue (46 mg, 0.12 mmol) weighed from the obtained residue (77 mg, 0.2 mmol) were added 101 potassium carbonate (82 mg, 0.59 mmmol), 219 potassium iodide (2.0 mg, 0.012 mmol), 97 N,N-dimethylformamide (1.5 mL) and 220 4-bromotetrahydropyran (33 muL, 0.30 mmol) and the mixture was stirred at 100C overnight. The reaction mixture was neutralized with 0.1% aqueous trifluoroacetic acid solution, and purified by high performance liquid chromatography (water-acetonitrile, each containing 0.1% 41 trifluoroacetic acid) to give the 221 title compound (5 mg, 0.011 mmol, 9.2%). MS (ESI) m/z 470 (M+H)+, 25637-16-5

The synthetic route of 25637-16-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; EA Pharma Co., Ltd.; KOBAYASHI, Kaori; SUZUKI, Tamotsu; OKUZUMI, Tatsuya; (110 pag.)EP3412664; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 25637-16-5

As the paragraph descriping shows that 25637-16-5 is playing an increasingly important role.

25637-16-5, 4-Bromotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-Bromooxane (3.17 g, 19.2 mmol) was added drop wise to a stirred suspension of magnesium (466 mg, 19.2 mmol) and one crystal of iodine in THF (26 mL) at ambient temperature. The reaction mixture was stirred for 30 mm before it was cooled in an ice-water bath. 3-Fluoropicolinaldehyde (1.20 g, 9.59 mmol) was added drop wise. The reaction mixture was then stirred for 30 mm. The reaction mixture was quenched with saturated aqueous ammonium chloride (40 mL) and diluted with ethyl acetate (100 mL) and water (30 mL). The product was extracted into the organic phase before the layerswere separated. The aqueous layer was extracted with a second portion of ethyl acetate (50 mL), and the combined organics were dried over sodium sulfate. The volatiles were removed under reduced pressure. The cmde reaction material was purified using silica gel column chromatography. (3-Fluoropyridin-2-yl)(oxan-4-yl)methanol (1.47 g, 6.96 mmol, 73 % yield) was isolated as a colorless oil. ?H NMR (400 MHz, CDC13) 8.40-8.45 (m, 1H), 7.40-7.46 (m, 1H), 7.27-7.33 (m, 1H), 4.83-4.88 (m, 1H), 4.00 (td, J=2.14,11.37 Hz, 2H), 3.36 (ddt, J=2.20, 9.23, 11.77 Hz, 2H), 1.90-2.03 (m, 1H), 1.65-1.78 (m,1H), 1.57 (dq, J=4.65, 12.47 Hz, 1H), 1.39-1.49 (m, 2H)., 25637-16-5

As the paragraph descriping shows that 25637-16-5 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; QUESNELLE, Claude A.; HARIKRISHNAN, Lalgudi S.; HILL, Matthew D.; (180 pag.)WO2016/183114; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 25637-16-5

As the paragraph descriping shows that 25637-16-5 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

Step A: Preparation of Intermediate 4-(4-Bromophenylthio)-tetrahydro-2H-pyran.To a solution of 4-bromobenzenethiol (300 mg, 1.60 mmol) in DMF (3 mL) was added sodium hydride (60% dispersion in mineral oil) (95 mg, 2.38 mmol) and 4-bromo-tetrahydro- 2H-pyran (458 mg, 1.75 mmol). The resulting mixture was stirred for 18 h at room temperature. The reaction was diluted with water and extracted twice with EtOAc. Purification by flash chromatography on silica gel (0-5% EtOAc in hexane) yielded the title compound (340 mg,78%) as a clear oil. 1H NMR (400 MHz, CDCl3) delta ppm 1.60 – 1.76 (m, 2 H), 1.92 (dd, J = 11.87, 1.52 Hz, 2 H), 3.20 – 3.33 (m, 1 H), 3.39 – 3.51 (m, 2 H), 3.93 – 4.05 (m, 2 H), 7.28 – 7.34(m, 2 H), 7.42 – 7.49 (m, 2 H)., 25637-16-5

As the paragraph descriping shows that 25637-16-5 is playing an increasingly important role.

Reference£º
Patent; ARENA PHARMACEUTICALS, INC.; WO2008/48609; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 25637-16-5

25637-16-5, 25637-16-5 4-Bromotetrahydropyran 13349654, aTetrahydropyrans compound, is more and more widely used in various fields.

25637-16-5, 4-Bromotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a round bottomed flask was added 4-(3-chloropyrazin-2-yloxy)aniline (1.2276 g, 5.54 mmol) dissolved in a mixtue of THF (8.86 mL) and NMP (2.215 mL). Iron(iii) acetylacetonate (0.098 g, 0.277 mmol) was added and the temperature was brought to 0 0C. (Tetrahydro-2H-pyran-4-yl)magnesium chloride (8.31 mL, 6.65 mmol) was added dropwise to the reaction mixture. Upon completion, the reaction was quenched with saturated ammonia chloride solution. The reaction mixture was diluted with water and extracted with EtOAc. The organic extract was washed with water, brine, dried with magnesium sulfate, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (120 g), eluting with a gradient of 10% to 100% EtOAc in hexane, to provide 4-(3-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)aniline.

25637-16-5, 25637-16-5 4-Bromotetrahydropyran 13349654, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; AMGEN INC.; ALLEN, Jennifer R.; BOURBEAU, Matthew P.; CHEN, Ning; HU, Essa; KUNZ, Roxanne; RUMFELT, Shannon; WO2010/57121; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics