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

Add 4-oxo-5- (p-tolyl) -1,4-dihydropyridazine-3-carboxylic acid ethyl (1.15 g, 4.452 mmol, 1.0 eq) and 4-bromotetrahydro-2H-pyran ( 882.0mg, 5.343mmol, 1.2eq) was dissolved in N, N-dimethylformamide (10.0mL), cesium carbonate (4.352g, 13.356mmol, 3.0eq) was added, and the temperature was raised to 100 C for 2h. TLC showed the reaction After completion, the reaction solution was filtered and concentrated under reduced pressure to remove N, N-dimethylformamide. Ethyl acetate was added, washed four times with water, dried, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (DCM: MeOH = 200: 1). ~ 30: 1) to obtain the product (1.0g, yield: 87.0%).

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

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

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

General procedure: A mixture of {(S)-6-[(R)-7-fluoro-4-(4-hydroxy-phenoxy)-indan-1 -yloxy]-2,3-dihydro- benzofu ra n-3-yl}-acetic acid methyl ester (60 mg), toluene-4-su lfon ic acid 2-methoxy- ethyl ester (34 mg), and cesium carbonate (60 mg) in N,N-dimethylformamide (2 mL) is stirred for 1.5 h at 6000. After cooling to room temperature, the mixture is dilutedwith water an extracted with ethyl acetate. The combined extracts are washed with brine, dried (MgSO4), and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20-*60:40) to give the title compound. The title compound is prepared from {(S)-6-[(R)-4-(4-cyano-3-hydroxy-phenoxy)-7- fluoro-indan-1 -yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester and 4- bromo-tetrahydropyran following a procedure analogous to that described forIntermediate 8. The crude product is used for the next reaction step without further purification.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; LANGKOPF, Elke; WAGNER, Holger; WO2014/86712; (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

25637-16-5, Step 1: To a solution of Core B (700.00 mg, 2.84 mmol, 1.00 eq) in MeCN (14 mL) was added CS2CO3 (1.85 g, 5.68 mmol, 2.00 eq) at 0C. After 30 min, 4- 0242952445-01 bromotetrahydropyran (703.03 mg, 4.26 mmol, 1.50 eq) was added. The mixture was stirred at 100C for 16 h in a sealed tube. The reaction mixture was filtered and the filtrate was concentrated. The crude product was purified by prep-HPLC (TFA) to give compound 39_6 (45.0 mg, 136.18 mupiiotaomicron, 4.8% yield) as a yellow solid. LCMS: RT = 0.702 min, mlz 331.1 [M+H]+ NMR (CDCb, 400 MHz) delta 8.42-8.40 (d, / = 5.6 Hz, 1H), 7.94 (s, 1H), 7.11- 7.10 (d, / = 5.2 Hz, 1H), 4.37-4.33 (m, 1H), 4.19-4.15 (m, 1H), 3.59-3.54 (m, 2H), 3.28- 3.26 (d, / = 6.4 Hz, 2H), 2.6 (s, 3H), 2.44-2.40 (m, 2H), 1.87-1.84 (m, 2H), 1.05-1.02 (m, 1H), 0.55-0.50 (m, 2H), 0.33-0.30 (m, 2H).

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

Reference£º
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD; BEN NERIAH, Yinon; BRACHYA, Guy; BURSTAIN, Ido; MINZEL, Waleed; SNIR-ALKALAY, Irit; VACCA, Joseph; LI, Dansu; (129 pag.)WO2017/21969; (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

To a suspension of magnesium (24.3 g, 1.00 mol) in THF (500 mL) was added three crystals of iodine followed by dropwise addition of neat 4-bromotetrahydro-2H-pyran (100g. 607 mmoL) through an additional funnel under N2, during which the inner temperature was controled under 45 C. The reaction mixture was continued stirring for 2 h at ambient temperature. The reaction mixture was cooled to – 30 C followed by dropwise addition of 3-fluoropicolinaldehyde (50.3 g, 402 mmoL) in THF (300 mL) through an additional funnel, during which the inner temperature was kept between -20 C to -30 C. After 1 h, the reaction mixture was filtered through a thin pad of celite. To the filtrate was added sat. aq. NH4C1 (100 mL) and the two layers were seperated. The organic phase was dried over anhydrous Na2SO4 and collected by filtration and washing with EtOAc(200m1). The filtrate was concentrated on a rotary evaporator. The crude compound was purified using a reverse phase chromatography eluting with 4050 % MeCN in H20 to afford the racemic compound (52 g, 61 % yield), which was separated by chiral prep SFC to give Enantiomer a, (3 -fluoropyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol (Intermediate 1, 25.1 g, 29.6 % yield) and Enantiomer b, (3 -fluoropyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol (Intermediate 2, 25.3 g, 29.7 %).Enantiomer a (Intermediate 1): LC-MS [M+H]= 212. Chiral Chromatography Report: RT = 12.25 mm(Column: Chiralpak AY-H(ADHOCE-VCOO1 0.46×25 cm; Mobil Phase: 90/10/0.1 Hexane/EtOH/DEA; Flow:1.0 mL/min). ?H NMR (400 MHz, DMSO-d6) 8.42 (dd, J = 3.20, 1.32 Hz, 1H), 7.66 (ddd, J = 9.8, 8.36, 1.12Hz, 1H), 7.35-7.42 (m, 1H), 5.23 (d, J = 6.52 Hz, 1 H), 4.52 (dd, J = 7.32, 7.28 Hz, 1H), 3.88 (dd, J = 11.4,2.92Hz, 1H), 3.75 (dd, J = 11.2, 3.02 Hz, 1H), 3.26 (dt, J = 12.0, 2.04 Hz, 1H), 3.17 (dt, J = 11.8, 2.24 Hz, 1H), 2.01-2.12 (m, 1H), 1.82 (dd, J= 13.3, 1.52 Hz, 1H), 1.24 -1.38 (m,1H), 1.12- 1.24 (m, 1H), 1.00 (dd, J 12.9, 1.34,1H).

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

Reference£º
Patent; JACOBIO-BETA PHARMACEUTICALS CO., LTD.; JACOBIO-ALPHA PHARMACEUTICALS CO., LTD.; JACOBIO PHARMACEUTICALS CO., LTD.; FANG, Haiquan; ZHOU, Wenlai; HU, Shaojing; CHEN, Mingming; YANG, Guiqun; WANG, Yanping; DU, Yuelei; LI, Qinglong; WU, Tong; WU, Lingjun; LI, Haijun; LONG, Wei; (179 pag.)WO2019/80941; (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

Magnesium (86.5 mg, 3.60 mmol) was stirred vigorously under nitrogen for 30 min. THF (2 mL) and dibromoethane (2 drops) were added and the reaction mixture was warmed to 50 C. A solution of 4-bromotetrahydropyran (495 mg, 3.00 mmol) in THF (4 mL) was added drop-wise over 5 min and the reaction mixture was heated at reflux for 2 h. A solution of 3-chloro-4-pyridaldehyde (170 mg, 1.20 mmol) in THF (4 mL) was added drop-wise over 5 min and the reaction mixture was heated at reflux for 6 h, stirred at room temperature overnight and heated at reflux for 8 h. The reaction mixture was cooled to 0 C. and quenched with sat aq NH4Cl (10 mL). The reaction mixture was diluted with EtOAc (40 mL) and the aqueous fraction was extracted with EtOAc (3*40 mL). The combined organic fractions were washed with sat aq Na2CO3 (20 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by normal phase column chromatography to give the crude title compound as a pale yellow gum (69.0 mg, 25%). LCMS (ES+): 228.2 (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; PROXIMAGEN LIMITED; Evans, David; Carley, Allison; Stewart, Alison; Higginbottom, Michael; Savory, Edward; Simpson, Iain; Nilsson, Marianne; Haraldsson, Martin; Nordling, Erik; Koolmeister, Tobias; US2013/102587; (2013); 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 4-bromotetrahydro-2H-pyran (50.0 g, 303 mmol, 1.0 eq) in DMF (300 mL) under a N2 atmosphere was added KSAc (41.5 g, 364 mmol, 1.2 eq) and the mixture was stirred at RT overnight. The mixture was diluted with water (700 mL) and extracted with EtOAc (200 mL*3). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to afford the title compound (41.5 g, 68%) as a brown oil. 1H NMR (400 MHz, CDCl3) delta 3.91-3.87 (m, 2H), 3.71-3.64 (m, 1H), 3.57-3.51 (m, 2H), 2.31 (s, 3H), 1.92-1.88 (m, 2H), 1.71-1.62 (m, 2H)., 25637-16-5

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

Reference£º
Patent; Ribon Therapeutics Inc.; Schenkel, Laurie B.; Vasbinder, Melissa Marie; Kuntz, Kevin Wayne; Swinger, Kerren Kalai; (179 pag.)US2019/194174; (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.

Step a) Intermediate 200 -[(4-Bromophenyl)sulfanyl]tetrahydro-2H-pyran To a solution of 4-bromobenzenethiol (2 g, 10.58 mmol) in DMF (20 ml) was added NaH (0.635 g, 15.87 mmol) at 0 C and the reaction stirred for 1 h. To this was added 4-bromotetrahydro-2H-pyran (1.92 g, 1 1.64 mmol) in DMF and the reaction allowed to warm to r.t. and stirred for 67 h. Reaction was quenched by addition of water and extracted with EtOAc (x 2). The organics were washed with brine (x 5), dried (MgSC>4) and concentrated under reduced pressure. The residue was purified by column chromatography (Si02; 0 -100 % DCM in petrol) to yield 4-[(4- bromophenyl)sulfanyl]tetrahydro-2H-pyran (2.18 g, 75 %). ? NMR (400 MHz, DMSO- ) 87.52 (ra, 2H), 7.35 (m, 2H), 3.73 – 3.88 (m, 2H), 3.44 – 3.56 (m, 1H), 3.39 (m, 2H), 1.84 (m, 2H), 1.49 (m, 2H)

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

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; RUPRAH, Parminder, Kaur; MERCHANT, Kevin, John; WALSH, Louise, Marie; KERR, Catrina, Morven; FIELDHOUSE, Charlotte; HARRISSON, David; MAINE, Stephanie; HAZEL, Katherine; WO2013/27001; (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.

Preparation 203,6-Dihydro-2H-pyran4-Bromotetrahydropyran (20 g, 121 mmol) and 5 N sodium hydroxide (30 mL) are stirred and heated at 90 C for 18 h. The mixture is cooled to room temperature and the organic layer is separated from the aqueous. The organic layer, containing product only, is poured into a pre-weighed flask containing sodium sulfate for drying, which yields the title compound as a pale yellow oil (9.99 g, 98%). The title compound is stored over sodium sulfate as volatility prevents any filtering, rinsing, and concentration in vacuo. 1H NMR (400 MHz, DMSO-de) delta 5.78-5.74 (m, 1H), 5.69-5.66 (m, 1H), 3.96-3.94 (m, 2H), 3.61 (t, J= 5.5 Hz, 2H), 2.01-1.99 (m, 2H).

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

Reference£º
Patent; ELI LILLY AND COMPANY; JADHAV, Prabhakar Kondaji; SAEED, Ashraf; GREEN, Jonathan Edward; KRISHNAN, Venkatesh; MATTHEWS, Donald Paul; STEPHENSON, Gregory Alan; WO2013/55577; (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.

To a solution of [4-(7-Hydroxymethoxyquinazolin-4-yl)piperidin-l-yl][4- (trifluoromethoxy)phenyl]methanone (100 mg, 0.24 mmol) in 1 mL of N,N-dimethyl formamide were added potassium iodide, (41 mg, 0.3 mmol) and 4-(bromomethyl)-tetrahydro-2H-pyran, 119 mg (0.72 mmol). The resulting solution was stirred 12 h at 80C. After chromatography, the title compound was obtained as a brown solid (24 mg, 26%). After filtration, removal of the solvent and susequent chromatography, the product was obtained as a white solid in 10% yields (12 mg). MS (ESIpos): m/z = 502 (M+H)+; LC-MS[Method 2] : R, = 1.52 min; 1H-NMR (400 MHz, DMSO -d6) d 1.63-1.72 (m, 2H), 1.86-1.90 (m, 4H), 2.06-2.09 (m, 2H), 3.07-3.08 (m, 1H), 3.56 (t, 2H), 3.68-3.69 (m, 1H), 3.88 (t, 2H), 3.96-3.99 (m, 1H), 4.61-4.62 (m, 2H), 4.90-4.94 (m, 1H), 7.36 (d, 1H), 7.44-7.46 (m, 3H), 7.59 (d, 2H), 8.38 (d, 1H), 9.09 (s, 1H).

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; NGUYEN, Duy; WORTMANN, Lars; FARIA ALVARES DE LEMOS, Adelaide, Clara; BOeMER, Ulf; SUeLZLE, Detlev; HOLTON, Simon; LECHNER, Christian; (147 pag.)WO2019/170543; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics