Category: 25637-16-5

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

K2C03 (0.16 g, 1 .20 mmol) followed by ethyl iodide (0.07 mL, 0.90 mmol) were added at RT to a solution of compound 67b (0.20 g, 0.60 mmol) in dry DMF (7 mL) and the reaction mixture was stirred at RT for 48 h. Crushed ice was added and the mixture was extracted with EtOAc. The organic phase was washed with water and brine, dried over Na2S04 and evaporated. The residue was purified by flash column chromatography [silica; hexane with 5% EtOAc]. White solid. Yield: 0.15 g (69%). HPLC (method 1 ): Rt = 2.67 min, m/z [M+H]+ = 362.0 (MW calc. 361.41 ). H NMR (400 MHz, DMSO-d6, delta ppm): 8.82 (s, 2H), 8.03 (d, 1 H, J = 1.96 Hz), 7.68-7.64 (m, 1 H), 7.48-7.43 (m, 1 H), 7.38-7.32 (m, 2H), 6.71 (d, 1 H, J = 8.1 Hz), 6.50-6.48 (m, 1 H), 4.22 (s, 2H), 4.03-3.98 (m, 2H), 1 .35-1 .32 (m, 3H), 1.10-1.02 (m, 4H).Prepared from compound 67b and 4-bromotetrahydro-2H-pyran in analogy to procedure 67c. White solid. Yield: 10 mg. MS: m/z: [M+H] = 418.1 (MW calc. 417.19)., 25637-16-5

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

Reference£º
Patent; GRUeNENTHAL GMBH; KONETZKI, Ingo; JAKOB, Florian; WAGENER, Markus; WELBERS, Andre; HESSLINGER, Christian; (138 pag.)WO2017/108203; (2017); 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.

5- (4-Fluorophenyl) -4-oxo-1,4-dihydropyridazine-3-carboxylic acid ethyl ester (500.0 mg, 1.9 mmol, 1.0 eq) was dissolved in DMF (5 mL) and added Cesium carbonate (1.85 g, 5.70 mmol, 3.0 eq) and 4-bromotetrahydro-2H-pyran (628.7 mg, 3.81 mmol, 2.0 eq) were stirred at 120 C for 5 hours. The reaction was monitored by TLC, and the reaction was concentrated under reduced pressure. Ethyl acetate (15 mL) and water (20 mL) were added, and the layers were separated. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate). Esters = 8: 1 to 2: 1) to obtain the product (342.0 mg, yield: 51.9%).

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; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Li Lin; Wan Zhonghui; (107 pag.)CN110041316; (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.

To a solution of 4-bromopyridin-2-ol (1 g, 5.75 mmol) in DMF (10 mL), stirring at rt, was added, potassium fert-butoxide (0.677 g, 6.03 mmol) . The mixture was stirred for 30 min then 4- bromotetrahydro-2H-pyran ( 1.423 g, 8.62 mmol) was added, and the resulting mixture was stirred at 70 C for 2 h. The mixture was cooled to rt, diluted with EtOAc (50 mL) and quenched with water (20 mL). The organic layer was washed with water (2×20 mL), brine (20 mL), dried over anhydrous MgS04 and filtered. The filtrate was concentrated in vacuo to afford the title compound (0.13 g, 9%); LC/MS (Table 1, Method f) Rt = 0.74 min; MS m/z: 258, 260 (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; ABBVIE INC.; BREINLINGER, Eric, C.; COX, Phil, B.; DAANEN, Jerome; DIETRICH, Justin; DJURIC, Stevan; DOMBROWSKI, Amanda, W.; FRANK, Kristine, E.; FRIEDMAN, Michael, M.; GOMTSYAN, Arthur; LI, Huan-Qui; LONGENECKER, Kenton; OSUMA, Augustine; ROWLEY, Ann, Marie; SCHMIDT, Robert; VASUDEVAN, Anil; WILSON, Noel; (378 pag.)WO2016/168641; (2016); 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.

General procedure: To a cooled solution of compound 6 (361.0 mg, 1 mmol) in DMF (10 mL) was added NaH (60% in oil, 48.0 mg, 1.2 mmol) carefully. The mixture was stirred at 0 C for 1h. A solution of R1X (X=Cl, Br; 1.2 mmol) in DMF (5 mL) was then added dropwise in the mixture. The mixture was heated to 40 C and stirred for 8-16 h. The reaction mixture was cooled and quenched at 0 C with a saturated NH4Cl aqueous solution. Then mixture was concentrated under vacuum to remove most of the DMF and re-dissolved with CH2Cl2. After filtering, the filtrate was washed with saturated NaCl aqueous solution, dried with MgSO4 and concentrated under vacuum. The crude material was purified by column chromatography (PE/EA) on silica gel to afford compound 6a-6r., 25637-16-5

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

Reference£º
Article; 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; European Journal of Medicinal Chemistry; vol. 183; (2019);,
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.

Step 2: 2-Methoxy-1-(tetrahydro-2H-pyran-4-yl)ethanoneA dry 50 mL flask under nitrogen was charged with magnesium (197 mg, 8.11 mmol) and a crystal of iodine. The solids were stirred vigorously while being warmedwith the heat gun to aerosolize the iodine. Upon cooling to room temperature, it was treated with THF (4 mL). The mixture was warmed with a heat gun and treated with a solution of 4-bromotetrahydro-2H-pyran (0.678 mL, 6.08 mmol) in THF (4 mL) dropwise via a dry addition funnel. When addition was complete, the mixture was placed in a preheated oil bath, and the mixture held at reflux for 30 mm. After cooling to room temperature, the solution was transferred to a stirred solution of N,2-dimethoxy-N- methylacetamide (270 mg, 2.03 mmol) in THF (12 mL) at -78 C. After stirring for 5 mm, the ice bath was removed and the reaction allowed to warm to room temperature. The reaction was placed in a 0 C bath, quenched by addition of sat. aq. ammoniumchloride, concentrated, diluted with EtOAc, washed with water, then brine, dried over magnesium sulfate, filtered, and concentrated to give 260 mg (81%) as clear oil. Material was used without purification. ?H NMR (400 MHz, CDC13) oe 4.1 1(s, 2H), 4.05-4.0(m, 2H), 3.5-3.44(m, 2H), 3.45(s, 3H), 2.8(m, 1H), 1.64(m, 2H), 1.32(m, 2H).

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; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (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.

4,4?-Di-tert-butyl-2,2?-bipyridine (8.05 mg, 0.03 mmol) and 1,2-dimethoxyethane- dichloronickel (1:1) (5.49 mg, 0.025 mmol) were charged under argon in a flask and suspended in dry 1,2-dimethoxyethane(2 ml). This mixture was sonicated for 5 mm. In a separated microwave vial under argon Iridium( 1+), [4,4?-bis( 1,1 -dimethylethyl)-2,2?-bipyridine-icNl ,icNl ?]bis [3 ,5-difluoro-2- [5-(trifluoromethyl)-2-pyridinyl-icN]phenyl-icC]-, (OC-6-33)-, hexafluorophosphate(1-) (1:1) (CAS 870987-63-6) (5.61 mg,5.00 jimol), N-[5-(7-bromo-4-oxoquinazolin-3 (4H)-yl)-2-(trifluoromethoxy)phenyl] -1 -(4-methylpiperazin-1 -yl)cyclopropanecarboxamide (56.6 mg, 100 jimol), and lithium hydroxide (4.79 mg,200 jimol) were dissolved in 1,2-dimethoxyethane (0.6 ml) and 4-bromotetrahydro-2H-pyran (17 jil, 150 jimol) and 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane (31 jil, 100 jimol) were added under argon. 0.4 ml of the solution of the first flask (catalyst mix) was added to the microwave vial mixture and an argon stream was passed through the resulting mixture for 10 mm. The reaction mixture was irradiated with one 34 W blue LED lamp in the EvoluChemTM PhotoChemistry Device using the 8 x 2 mL vialrack which contains an incorportated fan for cooling to maintain experiment at room temperature. The reaction mixture was then allowed to stir in the device for 15 hours. The reaction mixture was then charged completely on a silica gel column and a chromatographic separation was performed with a gradient of dichloromethane/methanol from 100:0 to 90:10. The material obtained was then purified by preparative RP-HPLC on a 125x30mm with acetonitrile/water (0.2% ammonia) to obtain 25.5 mg (97 % purity, 43 % yield) of the title product.LC-MS (Method 6): R = 1.18 mm; MS (ESIpos): m/z = 572 [M+H]1HNMR (400 MHz, DMSO-d6) [ppm]: -0.008 (2.71), 0.008 (2.39), 1.102 (1.40), 1.115 (3.81), 1.123(4.40), 1.132 (2.09), 1.235 (2.04), 1.245 (4.39), 1.252 (3.56), 1.265 (1.45), 1.714 (0.41), 1.736 (1.31),1.747 (1.12), 1.764 (3.86), 1.774 (5.09), 1.787 (3.43), 1.795 (3.34), 2.157 (0.78), 2.195 (16.00), 2.328(0.72), 2.332 (0.60), 2.366 (0.69), 2.454 (6.05), 2.670 (0.59), 2.980 (0.65), 2.992 (0.73), 3.004 (1.08),3.018 (0.76), 3.030 (0.50), 3.449 (1.27), 3.460 (1.13), 3.477 (2.36), 3.485 (2.44), 3.504 (1.21), 3.512(1.41), 3.972 (2.94), 3.979 (2.01), 3.998 (2.13), 7.366 (2.14), 7.372 (2.14), 7.388 (2.37), 7.394 (2.50),7.531 (2.02), 7.535 (2.22), 7.552 (2.12), 7.555 (2.45), 7.597 (4.28), 7.675 (1.83), 7.679 (1.89), 7.697(1.67), 7.701 (1.58), 8.122 (3.87), 8.142 (3.56), 8.346 (8.33), 8.356 (0.44), 8.582 (3.80), 8.588 (3.82), 10.651 (3.83)., 25637-16-5

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

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; JIMENEZ, NUNEZ, Eloisa; BORISSOFF, Julian; HAHN, Michael; DIETZ, Lisa; ZDENKA, GAUGAZ, Fabienne; BENDER, Eckhard; LANG, Dieter; GIESE, Anja; THEDE, Kai; ZORN, Ludwig; BOULTADAKIS ARAPINIS, Melissa; (190 pag.)WO2019/63708; (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.

Cesium carbonate (33.6 mmol), 3-amino-5-bromo-1H-pyrazole-4-carbonitrile (22.4 mmol) and bromocyclopentane (2.64 mL, 24.6 mmol) in MeCN (170 mL) was stirred at 80 C for 19 h, then cooled to RT and partitioned between water and EtOAc. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification gave the titled compound (1.00g, 3.92 mmol, 18% yield). UPLC-MS(ES, Short acidic): 1.58 mi mlz 256.9 [M+2], 25637-16-5

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

Reference£º
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (266 pag.)WO2017/103611; (2017); 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

Example 1384-[4-(2-methoxyphenyl)piperazin- I -yl]-1 -(tetrahydro-2H-pyran-4-yl)- I Hpyrazolo[ 3, 4-d]pyrimidine To 100 mg (0.32 mmo[) 4-[4-(2-methoxypheny[)piperazin-1 -y[]-1 H-pyrazo[o[3,4- d]pyrimidine, 525mg (1.61 mmo[) cesium carbonate and 12.3 mg (0.08 mmo[) sodium iodide in 4 mL anhydrous DMF were added 160 mg (0.97 mmo[) 4-bromotetrahydro- 2H-pyran. It was stirred over night at rt and then 4 h at 50CC. The mixture was concentrated on a rotavap. 20 mL water and 15 mL dich[oromethane were added.The [ayers were separated and the aqueous phase was extracted three times with dich[oromethane. The combined organic phases were washed with brine, dried over magnesium su[fate and concentrated. The residue was purified by HPLC yie[ding 44 mg (34%) product.LC-MS (ana[ytica[ method 3): R = 1.14 mm, MS (ESipos): mlz = 395 (M+H).1H-NMR (300MHz, DMSO-d6): 6 [ppm]= 1.76 – 1.87 (m, 2H), 2.05 – 2.22 (m, 2H), 3.05 -3.14 (m, 4H), 3.47 – 3.60 (m, 2H), 3.82 (5, 3H), 3.94 – 4.03 (m, 2H), 4.03 – 4.11 (m,4H), 4.85 -4.99 (m, 1H), 6.84- 7.03 (m, 4H), 8.28 (5, 1H), 8.33 – 8.38 (m, 1H)., 25637-16-5

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

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; MUeLLER, Thomas; GOLZ, Stefan; TELSER, Joachim; REHWINKEL, Hartmut; SIEBENEICHER, Holger; BUCHMANN, Bernd; ZORN, Ludwig; EIS, Knut; KOPPITZ, Marcus; LINDNER, Niels; HEROULT, Melanie; NEUHAUS, Roland; WO2013/182612; (2013); 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.

25637-16-5, Step 1: (4-Fluorophenyl)(tetrahydro-2H-pyran-4-yl)methanolTo a 40 mL vial containing magnesium (0.39 g, 16.1 mmol) in THF (15 mL) was slowly added 4-bromotetrahydro-2H-pyran (PharmaBlock, 1.8 mL, 16.1 mmol) coolingin a water bath as needed. The resulting reaction mixture was stirred at room temperature for 1.5 h and then cooled in a water bath. 4-Fluorobenzaldehyde (Aldrich, 1.2 mL, 10.7 mmol) was added slowly. The resulting orange reaction mixture was removed from the water bath and quenched with sat. NH4C1 after 10 mm. 10% LiC1 solution was added and the mixture was extracted with Et20 (2x). The organic layer was dried over MgSO4,filtered and concentrated. The residue was purified using ISCO silica gel chromatography (80 g column, gradient from 0% to 50% EtOAc/hexanes) to give the title compound (1.12 g, 33%) as a colorless oil. ?H NMR (500 MHz, CDC13) oe 7.31 – 7.27 (m, 2H), 7.08 – 7.02 (m, 2H), 4.37 (dd, J=7.7, 2.4 Hz, 1H), 4.06 – 3.99 (m, 1H), 3.94 – 3.87 (m, 1H), 3.37 (td,J=11.9, 2.2 Hz, 1H), 3.29 (td,J=11.8, 2.3 Hz, 1H), 1.94- 1.87 (m, 2H),1.81 (tdt, J=1 1.6, 7.7, 3.8 Hz, 1H), 1.45 (qd, J=12.3, 4.7 Hz, 1H), 1.36 – 1.27 (m, 1H),1.16 (ddq, J=13.2, 3.9, 2.0 Hz, 1H); LCMS (M+H-H20) = 193.1; HPLC RT = 1.65 mill(Column: Chromolith ODS S5 4.6 x 50 mm; Mobile Phase A: 10:90 MeOH:water with0.1% TFA; Mobile Phase B: 90:10 MeOH :water with 0.1% TFA; Temperature: 40 C;Gradient: 0-100% B over 4 mm; Flow: 4 mL/min).

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (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.

234b) Ethyl 1 -(2,-fluoro-3′-((tetrahydro-2H-pyran-4-yl)oxy)-[1 ,1 ‘-biphenyl]-3-yl)-5-(2- (1 -methyl-1 H-1 ,2,3-triazol-4-yl)cyclopropyl)-1 H-pyrazole-4-carboxylate To a solution of ethyl 1 -(2′-fluoro-3’-hydroxy-[1 ,1 ‘-biphenyl]-3-yl)-5-(2-(1 -methyl-1 H-1 ,2,3- triazol-4-yl)cyclopropyl)-1 H-pyrazole-4-carboxylate (450 mg, 1 .006 mmol) in N,N- dimethylformamide (DMF) (5 mL) was added Cs2C03 (655 mg, 2.01 1 mmol) and 4- bromotetrahydro-2H-pyran (232 mg, 1 .408 mmol). It was heated in Microwave at 120 C for 2 h. The reaction mixture was diluted with water and extracted with ethyl acetate (2 x 30 mL). The combined organic layer was washed with chilled water (3 x 30 mL) and then brine solution (30 mL), dried over anhydrous Na2S04 and concentrated. The crude residue was purified by column chromatography eluting with 1 % methanol in DCM. Desired fractions were concentrated to give the title compound (200 mg, 0.217 mmol, 21 .58 % yield). LC-MS m/z 532.23 (M+H)+, 2.36 min (ret. time)., 25637-16-5

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

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; CALLAHAN, James Francis; KERNS, Jeffrey K.; LI, Peng; LI, Tindy; MCCLELAND, Brent W.; NIE, Hong; PERO, Joseph E.; DAVIES, Thomas Glanmor; GRAZIA CARR, Maria; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; NORTON, David; VERDONK, Marinus Leendert; WOOLFORD, Alison Jo-Anne; WILLEMS, Hendrika Maria Gerarda; (664 pag.)WO2017/60854; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics