Category: 25637-16-5

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.

General procedure: To a flame-dried Schlenk tube was charged with vinyl bromide (0.30 mmol, 2 equiv, if solid), unactivated alkyl halide (0.15 mmol, if solid), zinc powder (16.5 mg, 0.30 mmol, 2 equiv), and MgCl2 (14.2 mg, 0.15mmol, 1 equiv). The tube was moved into a dry glovebox, at which point Ni(cod)2 (2.1 mg, 0.008 mmol, 5 mol%) was added. The tube was capped with a rubber septum, and it was moved out of the glovebox. At this point, the vinyl bromide (0.30 mmol, 2 equiv, if liquid) and alkylhalide (0.15 mmol, 1 equiv, if liquid) were added together with solvent (1 mL) and pyridine (11.8 mg, 0.15 mmol, 1 equiv) via a syringe.The mixture was stirred for 16 h under N2 atmosphere at 25 C, and then it was directly loaded onto a column (silica gel) without work-up. The residue in the reaction vessel was rinsed with small amount of CH2Cl2. Flash column chromatography provided the product as a solid or oil. The E/Z ratio of the product was determined by GC-MS. (E)-4-Styryl-1-tosylpiperidine (3): according to the general procedure, column chromatography (silica gel, 7% EtOAc/PE) gave the product (42.5 mg, 0.125 mmol, 83%) as a white solid; mp 140-141 C. 1H NMR (500 MHz, CDCl3): delta = 7.66 (d, J = 8.0 Hz, 2 H), 7.34-7.28 (m, 6 H), 7.20 (t, J = 7.0 Hz, 1 H), 6.31 (d, J = 16.0 Hz, 1 H), 5.97 (dd, J = 7.0,16.0 Hz, 1 H), 3.82-3.80 (m, 2 H), 2.44 (s, 3 H), 2.34-2.29 (m, 2 H), 2.08-2.02 (m, 1 H), 1.83-1.81 (m, 2 H), 1.73-1.70 (m, 1 H), 1.46-1.39 (m, 1 H). 13C NMR (125 MHz, CDCl3): delta = 143.4, 137.1, 133.4, 133.1, 129.5, 128.9, 128.5, 128.2, 127.7, 127.2, 126.0, 46.1, 38.5, 31.2, 21.5. HRMS (ESI): m/z [M + H]+ calcd for C20H24NO2S: 342.1522; found: 342.1525.

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

Reference£º
Article; Gu, Jun; Qiu, Canbin; Lu, Wenbin; Qian, Qun; Lin, Kunhua; Gong, Hegui; Synthesis; vol. 49; 8; (2017); p. 1867 – 1873;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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.

General procedure: Sodium hydride (60% suspension in mineral oil, 31 mg, 0,76 mmol) is added to asolution of 36a (109 mg, 91 % content, 0,63 mmol) in DMF (1 mL) at 0C. After 20mi 2-(trimethylsilyl)ethoxymethyl chloride (157 p1, 0,88 mmol) is added dropwise tothe reaction mixture. After stirring for 1 h at rt, the reaction is diluted with EtOAc,washed with NaHCO3 satured solution and brine. The organic layer is separated and dried with a Phase separator cartridge and evaporated under vacuum to give a residue that is purified by flash chromatography (eluent 0-10% EtOAc/cyclohexane) to furnish the title compound (182 mg).UPLC-MS (Method 2): Rt = 1 .61MS (ESI pos): mlz = 288 (M+H)+

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; CUI, Yunhai; DOODS, Henri; FERRARA, Marco; JUST, Stefan; KUELZER, Raimund; LINGARD, Iain; MAZZAFERRO, Rocco; RUDOLF, Klaus; WO2014/184275; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

To a solution of 6 (300 mg, 1.60 mmol) in DMF (3 mL) was added sodium hydride (95 mg, 60% dispersion in mineral oil, 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 mixture was diluted with water (25 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The resultant residue was purified by column chromatography (0-5% gradient of EtOAc in hexane) to provide the title compound (340 mg, 78%) as a colouless oil. 1H NMR (400 MHz, CDCl3) 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

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

Reference£º
Article; Semple, Graeme; Santora, Vincent J.; Smith, Jeffrey M.; Covel, Jonathan A.; Hayashi, Rena; Gallardo, Charlemagne; Ibarra, Jason B.; Schultz, Jeffrey A.; Park, Douglas M.; Estrada, Scott A.; Hofilena, Brian J.; Smith, Brian M.; Ren, Albert; Suarez, Marissa; Frazer, John; Edwards, Jeffrey E.; Hart, Ryan; Hauser, Erin K.; Lorea, Jodie; Grottick, Andrew J.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 1; (2012); p. 71 – 75;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

To a cooled solution of 79 (0.5 g, 1.17 mmol, 1.0eq), and 79.1 (0.386 g, 2.34 mmol, 1.2 eq) inAcetonitrile (15mE) at 0 C. was added Cesium carbonate (0.9 g, 2.92mmol, 2.5 eq). The reaction was stirred at 70 C. for 2 h. Afier completion of reaction, reaction mixture was transferred into water and product was extracted with ethyl acetate. Organic layer was combined and dried over sodium sulphate and concentrated under reduced pressure to obtain crude material. This was further purified by column chromatography and compound was eluted in 20% ethyl acetate in hexane to obtain pure 79.2. (0.150 g, 25.06%). MS (ES):mlz 511.24 [M+H]., 25637-16-5

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

Reference£º
Patent; Nimbus Lakshmi, Inc.; Masse, Craig E.; Greenwood, Jeremy Robert; Mondal, Sayan; Cowen, Scott D.; McLean, Thomas H.; (624 pag.)US2019/31664; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

General procedure: In air, CuBr (7.1 mg, 0.05 mmol), PPh3 (17.03 mg, 0.065 mmol), LiOtBu(80 mg, 1mmol), and bis(neopentyl glycolato) diboron (168mg, 0.75 mmol ) were added to aSchlenk tube equipped with a stir bar. The vessel was evacuated and filled with argon(three cycles). DMAc (1 mL), alkyl halide (0.5 mmol) were added in turn by syringeunder an argon atmosphere (if the alkyl halide is a solid, it was added along with theCuBr). The resulting reaction mixture was stirred vigorously at 25 C for 18 h. Thereaction mixture was then diluted with EtOAc, filtered through silica gel with copiouswashings (petroleum ether to EtOAc), concentrated, and purified by columnchromatography., 25637-16-5

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

Reference£º
Article; Lou, Xin; Zhang, Zhen-Qi; Liu, Jing-Hui; Lu, Xiao-Yu; Chemistry Letters; vol. 45; 2; (2016); p. 200 – 202;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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.

Cesium carbonate (450 mg, 1.4 mmol) was added to a solution of N-(4-((7-hydroxy-6-methoxyquinazolin-4-yl)oxy)phenyl)-2-( 4-isopropyl-1H-1 ,2,3-triazol-1-yl)acetamide (20010 mg, 0.5 mmol) and 4-bromotetrahydro-2H-pyran (456 mg, 2.8 mmol) in DMF (3 mL) undernitrogen. The resulting mixture was stirred at 100C for 3 hours. The crude product waspurified by preparative HPLC. Fractions containing the desired product were combined andconcentrated under vacuum to afford the title compound as a white solid (124 mg, 52%). 1HNMR (400 MHz, DMSO-d6) 8 1.26 (6H, d), 1.61 – 1.75 (2H, m), 2.09 (2H, d), 2.95 – 3.0715 (lH, m), 3.57- 3.59 (2H, m), 3.86- 3.95 (2H, m), 3.98 (3H, s), 4.94- 4.96 (lH, m), 5.30 (2H,s), 7.25-7.33 (2H, m), 7.55 (2H, d), 7.64- 7.73 (2H, m), 7.90 (lH, d), 8.54 (lH, s), 10.59 (lH,s); m/z: ES+ [M+H]+ 519.

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

Reference£º
Patent; ASTRAZENECA AB; GRECU, Tudor; KETTLE, Jason, Grant; PACKER, Martin, John; PEARSON, Stuart, Eric; SMITH, James, Michael; (58 pag.)WO2018/197643; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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.

Added 3-bromotetrahydropuran (651 ul, 5.901 mmol) to a mixture of 3-methyl-4-nitro-1 H- pyrazole (500 mg, 3.934 mmol) and cesium carbonate (2.564 g, 7.868 mmol) in DMF (5 mL) and stirred at 70 C for 6 d. Added ether (50mL) and filtered off the residues. Removed the solvent from the filtrate in vacuo and purified the residue by flash chromatography on neutral alumina using methanol/dichloromethane (1/99) to give the titled compound (334 mg, 40%). LCMS (Method 1 ) Rt 2.042 min.

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

Reference£º
Patent; BIONOMICS LIMITED; HARVEY, Andrew John; RIPPER, Justin Anthony; HUFF, Belinda Cheryl; PAUL, Dharam; WO2015/123722; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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.

To a suspension of magnesium (24.3 g, 1.00 mol) in THF (500 mL) under N2 was added three iodine crystals,Then, dropwise pure 4-bromotetrahydro-2H-pyran (100g, 607mmoL),During the dropwise addition, the internal temperature is controlled to be lower than 45 C.The reaction mixture was stirred for a further 2 h at ambient temperature.The reaction mixture was cooled to -30 C, and then a solution of 3-fluoropyridaldehyde (50.3 g, 402 mmoL) in THF (300 mL) was added dropwise, and the internal temperature was maintained at -20 C to -30 C during the dropwise addition.After 1 h, the reaction mixture was filtered through a thin pad of diatomaceous earth.To the filtrate was added a saturated aqueous solution of NH4Cl (100 mL), and the layers were separated.The organic phase was dried over anhydrous Na2SO4 and the filtrate was collected. The filtrate was concentrated on a rotary evaporator.The crude compound was purified using reversed-phase chromatography, eluting with 40-50% MeCN in H2O, to obtain a racemic compound (52 g, 61% yield),It was separated by chiral preparation SFC to obtain enantiomer A (25.1 g, 29.6% yield)And enantiomer B (25.3 g, 29.7% yield)., 25637-16-5

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

Reference£º
Patent; Beijing Jiakesitu Drug Discovery Co., Ltd.; Beijing Jiakesi Drug Discovery Co., Ltd.; Fang Haiquan; Li Haijun; Yang Guiqun; Wang Yanping; Wu Lingjun; Li Qinglong; Du Yuelei; Zhang Lei; Hu Shaojing; (65 pag.)CN110407854; (2019); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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.

Compound 10-rac (100 mg, 0.28 mmol) and 37 4-bromotetrahydropyran (94 mg, 0.56 mmol) were dissolved in 5mL 31 DMF, and then the solution was added with 25 K2CO3 (78 mg, 0.56 mmol) and reacted at 90C for 40 h. After the reaction finished, the mixture was poured into water and extracted with EtOAc (40 mL¡Á3). The ethyl acetate layers were combined and washed with water and saturated salt solution, then dried over anhydrous sodium sulfate and filtered, and the filtrate was vacuum concentrated to give a crude product, which was purified by a preparation plate to give Compound 3a-rac (65 mg, 56.1% yield)., 25637-16-5

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

Reference£º
Patent; Ginkgo Pharma Co., Ltd.; CHEN, Li; ZHAI, Peibin; SHAO, Qing; WU, Jin; LI, Xiaowen; (46 pag.)EP3492467; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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.

[00497] To a solution of 122-1 (50.0 mg, 0.16 mmol, 1. 0 eq) in DMF (5.0 mL) was added K2C03 (45.23 mg, 0.33 mmol, 2.0 eq) and 122-2 (32.4 mg, 0.120 mmol, 1.2 eq). The mixture was stirred at 100 C for 24 hours under an N2 atmosphere. LCMS showed the desired compound was formed. The reaction was filtered to give a crude product. The crude product was purified by prep-HPLC to give the title compound (27.33 mg, 70.19 umol, 42.85% yield). LCMS (ESI): RT = 0.932 min, mass calc. for Ci9Hi8F3N50 389.15, m/z found 390.0[M+H]+; 1HNMR (400 MHz, CDCl3-i 9.08 (s, 1H), 8.21 (dd, J= 1.4, 7.9 Hz, 1H), 7.54 (d, J= 8.5 Hz, 3H), 7.41- 7.35 (m, 1H), 7.29 (d, J= 8.5 Hz, 2H), 7.05 (t, J= 7.3Hz, 1H), 5.07 – 4.95 (m, 1H), 4.16 (td, J= 3.3, 12.0 Hz, 2H), 3.64 (dt, J = 2.3, 11.5 Hz, 2H), 2.46 – 2.24 (m, 4H).

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

Reference£º
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (396 pag.)WO2018/204532; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics