Category: 125552-89-8

125552-89-8, 4-(Bromomethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Under argon atmosphere, a solution of the carbazole amide 67 (100mg, 0.36mmol), 1-bromo-3-methoxypropane (61muL, 0.54mmol), and Cs2CO3 (234mg, 0.72mmol) in DMF (10mL) was tightly capped in a 20mL microwave vessel. The mixture was subjected to microwave irradiation at 140C for 1h and then cooled to room temperature. The reaction mixture was diluted with EtOAc and filtered. The organic solvents were evaporated in vacuo. The residue was suspended in methyl tert-butyl ether (150mL), and the organic phase was washed with saturated aqueous sodium bicarbonate, brine, dried (MgSO4), filtered and evaporated in vacuo. The obtained residue was purified by column chromatography on silica gel eluting with EtOAc/heptanes in different proportions to give the title product (119mg, 95%) as a clear, colorless gum., 125552-89-8

125552-89-8 4-(Bromomethyl)tetrahydropyran 2773286, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Petrov, Ravil R.; Knight, Lindsay; Chen, Shao-Rui; Wager-Miller, Jim; McDaniel, Steven W.; Diaz, Fanny; Barth, Francis; Pan, Hui-Lin; Mackie, Ken; Cavasotto, Claudio N.; Diaz, Philippe; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 881 – 907;,
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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

A mixture of methyl 6-(2,6-difluoro-4-hydroxyphenyl)-5-fluoropicolinate (1.0 equiv.), 4-(bromomethyl)tetrahydro-2H-pyran (2.0 equiv.) and K2CO3 (4.0 equiv.) in DMF (0.20 M) was heated at 100 C. for 20 min in microwave. The reaction mixture was cooled off to rt and partitioned between EtOAc and H2O. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give methyl 6-(2,6-difluoro-4-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)-5-fluoropicolinate in 100% yield. LC/MS=382.0 (MH+), Rt=0.97 min., 125552-89-8

The synthetic route of 125552-89-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Burger, Matthew; Ding, Yu; Han, Wooseok; Nishiguchi, Gisele; Rico, Alice; Simmons, Robert Lowell; Smith, Aaron R.; Tamez, JR., Victoriano; Tanner, Huw; Wan, Lifeng; US2012/225061; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125552-89-8, 4-(Bromomethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 78 Preparation of 5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid [(S)-2,5-dioxo-1-(tetrahydro-pyran-4-ylmethyl)-pyrrolidin-3-yl]-amide Step1: Compound 75c (200 mg, 0.93 mmol), 60a (201 mg, 1.12 mmol), KI (163 mg, 0.98 mmol), K2CO3 (644 mg, 4.67 mmol) and acetonitrile (20 mL) were mixed in a microwave vial. The resulting mixture was reacted under microwave condition at 140 C. for 1 h. After being cooled, the mixture was filtered. The filtrate was evaporated and the residue was purified by column chromatography (EA::PE=1:3) to provide 78a(224 mg, 77%).

125552-89-8, As the paragraph descriping shows that 125552-89-8 is playing an increasingly important role.

Reference£º
Patent; Xcovery, Inc.; US2009/76005; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125552-89-8, 4-(Bromomethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[00547] Step B: To a mixture of tert-butyl ethyl(1-((1s,4s)-4-((1-methyl-6-oxo-1,6-dihydropyridazin-3-yl)oxy)cyclohexyl)-3-(1H-pyrazol-3-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (0.022 g, 0.041 mmol) and 4-(Bromomethyl)tetrahydropyran (0.015 g, 0.082 mmol) in DMA (0.4 mL) was added Cs2CO3 (0.028 g, 0.086 mmol) and the reaction was heated to 100 C. After 3 h, the reaction was cooled to room temperature and DCM (2 mL) was added and then TFA (5 mL) added. After 1 hr, the reaction mixture was concentrated and the resultant oil was resuspended in 1 mL of a solution of 60:40 ACN:water with 2% TFA modifier. The product was purified by C-18 HPLC (5-60% ACN in water with 0.2% TFA modifier). The product fractions were partitioned between aqueous NaHCO3 and DCM, extracted with DCM (2×15 mL), washed with brine (15 mL), dried over Na2SO4, filtered and concentrated to afford 6-(((1s,4s)-4-(6-(ethylamino)-3-(1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrazol-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)cyclohexyl)oxy)-2-methylpyridazin-3(2H)-one (0.0087 g, 0.015 mmol, 37 % yield) as a solid. Mass spectrum (apci) m/z = 533.2 (M+H). 1H NMR (CDCl3) delta 9.08 (s, 1H), 7.42 (d, J = 2.2 Hz, 1H), 7.02 (d, J = 9.8 Hz, 1H), 6.94 (d, J = 9.8 Hz, 1H), 6.78 (d, J = 2.4 Hz, 1H), 6.08 (s, 1H), 5.10 (m, 1H), 4.32 (tt, J = 11.5, 3.9 Hz, 1H), 4.07 (d, J = 7.2 Hz, 2H), 3.97 (m, 2H), 3.66 (s, 3H), 3.43-3.26 (m, 4H), 2.53-2.40 (m, 2H), 2.38-2.20 (m, 3H), 1.97-1.89 (m, 2H), 1.84-1.73 (m, 2H), 1.59-1.51 (m, 2H), 1.45-1.33 (m, 5H).

125552-89-8, The synthetic route of 125552-89-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125552-89-8, 4-(Bromomethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of N-(2-hydroxyethyl)-4-(2H-tetrazol-5-yl)benzenesulfonamide (200 mg, 0.743 mmol, Intermediate 17) in Lambda/,/V-dimethylformamide (10 ml_), potassium carbonate (205 mg, 1 .485 mmol, commercial source: RCP) was added followed by the addition of 4- (bromomethyl)tetrahydro-2H-pyran (159 mg, 0.88 mmol, commercial source: Aldrich) at 26 C. The reaction mixture was heated to 80 C for 8 h. Upon completion, the reaction mixture was cooled to 26 C and evaporated under reduced pressure. The crude was purified by column chromatography (silicagel 100-200 mesh), eluted with 5% methanol in dichloromethane. The pure fractions were concentrated under reduced pressure to afford N- (2-hydroxyethyl)-4-(2-((tetrahydro-2H-pyran-4-yl)methyl)-2H-tetrazol-5- yl)benzenesulfonamide (80 mg, 18%).1H NMR (400 MHz, DMSO-de) delta 8.28-8.24 (m, 2H), 7.98 (d, J = 8.6 Hz, 2H), 7.79-7.72 (m, 1 H), 4.73-4.65 (m, 3H), 3.88-3.80 (m, 2H), 3.38 (q, J = 6.1 Hz, 2H), 3.29-3.27 (m, 2H), 2.85 (q, J = 5.3 Hz, 2H), 2.35-2.23 (m, 1 H), 1.52-1.46 (m, 2H), 1.40-1.31 (m, 2H). MS m/z [M+H]+= 368.12.

125552-89-8, As the paragraph descriping shows that 125552-89-8 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ALEMPARTE-GALLARDO, Carlos; ENCINAS, Lourdes; ESQUIVIAS PROVENCIO, Jorge; (206 pag.)WO2019/34729; (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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

To a stirred suspension of 3-bromo-N-(4-ethyl-phenyl)-4-hydroxy-N-isobutyl-benzenesulfonamide (11, 2.20 g, 5.34 mmol)and Cs2CO3 (3.48 g, 10.7 mmol) in DMF (44 mL), was added 4-(bromomethyl)tetrahydropyran (1.15 g, 6.40 mmol). The reactionmixture was stirred at 80 C for 16 h, cooled to r.t. and quenchedwith water (5.0 mL). The reaction mixture was extracted withEtOAc (2 50 mL) and the organic phases were combined, washedwith a saturated solution of sodium carbonate, brine, dried overMgSO4 and concentrated to dryness. The residue was trituratedwith heptane and the solid obtained was collected by filtration anddried to a constant weight in a vacuum oven at 40 C to afford thetitle compound (2.36 g, 87%) as a white solid: UPLC-MS(tR 1.52 min, purity 100%), ESI m/z 510.11/512.11 (MH); 1HNMR (400 MHz, CDCl3) d 7.77 (d, J 2.3 Hz, 1H), 7.46 (dd, J 8.6,2.3 Hz, 1H), 7.21e7.09 (m, 2H), 7.04e6.93 (m, 2H), 6.87 (d, J 8.6 Hz,1H), 4.07 (ddd, J 11.6, 5.0, 1.8 Hz, 2H), 3.94 (d, J 6.4 Hz, 2H), 3.50(td, J 11.6, 2.1 Hz, 2H), 3.29 (d, J 7.3 Hz, 2H), 2.67 (q, J 7.6 Hz,2H), 2.19 (m, 1H), 1.83 (m, 2H), 1.67e1.49 (m, 2H), 1.26 (t, J 7.6 Hz,3H), 0.93 (d, J 6.6 Hz, 6H)., 125552-89-8

The synthetic route of 125552-89-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Lafitte, Guillaume; Parnet, Veronique; Pierre, Romain; Raffin, Catherine; Vatinel, Rodolphe; Musicki, Branislav; Tomas, Loic; Bouix-Peter, Claire; Ouvry, Gilles; Daver, Sebastien; Arlabosse, Jean-Marie; Boiteau, Jean-Guy; Gerfaud, Thibaud; Harris, Craig S.; Tetrahedron; vol. 74; 40; (2018); p. 5974 – 5986;,
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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

A mixture of 58 (3g, 16.75mmol) and potassium thioacetate CH3COSK (3.4g, 33.5mmol) in DMF (60mL) was stirred at 90C for 2h. The reaction mixture was poured into cold water and then extracted with ethyl acetate (3¡Á30mL). The combined organic layers were washed with water (3¡Á60mL) and brine (30mL), and then dried over anhydrous MgSO4 and evaporated to dryness. The crude product was purified by silica gel flash chromatography (eluting with ethyl acetate in petroleum ether 2-5%) to give the title compound 59 as a yellow oil, (1.8g, yield=69%). 1H NMR (400MHz, CDCl3) delta 3.94 (dd, J=11.6Hz, 4.4Hz, 2H), 3.36-3.33 (m, 2H), 2.81 (d, J=6.4Hz, 2H), 2.32 (s, 3H), 1.69-1.65 (m, 3H), 1.30 (qd, J=12.4Hz, 4.0Hz, 2H); LC/MS (ESI, m/z) 175.08 [M+H]+., 125552-89-8

As the paragraph descriping shows that 125552-89-8 is playing an increasingly important role.

Reference£º
Article; Wang, Beilei; Wu, Jiaxin; Wu, Yun; Chen, Cheng; Zou, Fengming; Wang, Aoli; Wu, Hong; Hu, Zhenquan; Jiang, Zongru; Liu, Qingwang; Wang, Wei; Zhang, Yicong; Liu, Feiyang; Zhao, Ming; Hu, Jie; Huang, Tao; Ge, Juan; Wang, Li; Ren, Tao; Wang, Yuxin; Liu, Jing; Liu, Qingsong; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 896 – 916;,
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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

4-(Bromomethyl)tetrahydropyran (97.6 mul; 0.74 mmol) is added to a mixture of methyl 5-[(4-ethylphenyl)isobutylsulfamoyl]-1H-indazole-7-carboxylate (280.0 mg; 0.67 mmol) and cesium carbonate (329 mg; 1 mmol) in 1-methyl-2-pyrrolidone (2.8 ml). The reaction medium is stirred at a temperature of 80 C. overnight. The crude product is filtered and then purified by preparative HPLC (C18 column, eluent: acetonitrile in water/0.1% of formic acid). The methyl 5-[(4-ethylphenyl)isobutylsulfamoyl]-1-(tetrahydropyran-4-ylmethyl)-1H-indazole-7-carboxylate (223.4 mg; 63%) is obtained in the form of a white solid. 1H NMR (DMSO-d6) delta: 0.85 (d, J=6.6 Hz, 6H), 1.18 (t, J=7.6 Hz, 3H), 1.25 (dt, J=11.1, 5.3 Hz, 4H), 1.33-1.55 (m, 1H), 1.86-2.12 (m, 1H), 2.60 (q, J=7.6 Hz, 2H), 3.18 (td, J=11.1, 3.6 Hz, 2H), 3.35 (s, 2H), 3.79 (dt, J=11.4, 3.3 Hz, 2H), 3.93 (s, 3H), 4.57 (d, J=7.2 Hz, 2H), 6.93-7.06 (m, 2H), 7.12-7.23 (m, 2H), 7.80 (d, J=1.7 Hz, 1H), 8.37 (d, J=1.9 Hz, 1H), 8.48 (s, 1H). MS: [M+H]=514

125552-89-8, 125552-89-8 4-(Bromomethyl)tetrahydropyran 2773286, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; GALDERMA RESEARCH & DEVELOPMENT; MUSICKI, Branislav; OUVRY, Gilles; THOREAU, Etienne; BOUIX-PETER, Claire; (85 pag.)US2017/342062; (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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

A mixture of (tert-butoxycarbonyl)-L-valine (3.64 g, 16.75 mmol), 4-(bromomethyl)tetrahydro-2H- pyran (3.00 g, 16.75 mmol) and NaHCO3 (2.81 g, 33.50 mmol) in DMF (30 mL) was stirred at 70 C for 12 hours under N2 atmosphere. The reaction mixture was diluted with H20 (100 mL) and extracted with MTBE (50 mL x 2). The combined organic layers were washed with brine (20 mL x 2), dried overNa2SO4, filtered and concentrated under reduced pressure to give (tetrahydro-2H-pyran-4-yl)methyl(tert-butoxycarbonyl)-L-valinate (5 g, yield 94.63%, pale yellow oil) which was used into the next stepwithout further purification. 1H NMR (400 MHz, CDCI3) O 5.01 (d, J = 8.4 Hz, 1H), 4.22 (dd, J = 8.8 Hz,4.8 Hz, 1H), 4.00-3.97 (m, 4H), 3.40 (t, J= 11.2 Hz, 2H), 2.16-2.11 (m, 1H), 1.96-1.90 (m, 1H), 1.63 (d, J= 13.2 Hz, 2H), 1.45 (s, 9H), 0.97 (d, J 6.4 Hz, 3H), 0.90 (d, J 7.2 Hz, 3H)., 125552-89-8

As the paragraph descriping shows that 125552-89-8 is playing an increasingly important role.

Reference£º
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; CARTER, David Scott; HALLADAY, Jason S.; JACOBS, Robert T.; LIU, Yang; PLATTNER, Jacob J.; ZHANG, Yong-Kang; WITTY, Michael John; (149 pag.)WO2017/195069; (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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

General procedure: To a solution of intermediate7(0.5 mmol)inDMFwere added carbon disulfide (0.30 mL, 5.0 mmol) and finely powdered potassium phosphate (0.21 g, 1.0 mmol). After stirring at rt for 30 min, the appropriate benzyl bromide, cyclohexyl bromide, or chloromethylpyridine hydrochloride(0.5 mmol)was added and stirring was continued for 2 h. The mixture was poured into ice-water (40 mL), and the solution was extracted with dichloromethane(15 mL ¡Á 3). The combined extracts were washed with saturated brine and dried overanhydrous sodium sulfate overnight. After evaporation of the solvent, the crude productwas purified by column chromatography using dichloromethane/methanol (95:5, v/v) as eluent to give final compounds 8a-q.

125552-89-8, 125552-89-8 4-(Bromomethyl)tetrahydropyran 2773286, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Zhang, Ying; Yang, Chao-Rui; Tang, Xue; Cao, Sheng-Li; Ren, Ting-Ting; Gao, Man; Liao, Ji; Xu, Xingzhi; Bioorganic and Medicinal Chemistry Letters; vol. 26; 19; (2016); p. 4666 – 4670;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics