Category: 125552-89-8

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.

Synthesis of methyl 6-(2,6-difluoro-4-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)-5-fluoropicolinate 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

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

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;; ; Patent; Burger, Matthew; Nishiguchi, Gisele; Machajewski, Timothy D.; Rico, Alice; Simmons, Robert Lowell; Smith, Aaron R.; Tamez, JR., Victoriano; Tanner, Huw; Wan, Lifeng; US2012/225062; (2012); 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 suspension solution of152F (30 mg, 0.089 mmol), 4-(bromomethyl)tetrahydropyran (16.73 mg, 0.093 mmol)and C52CO3 (43.5 mg, 0.133 mmol) in DMF (1 mL) was heated to 120 C for 20 mm and 140 C for 1 h under microwave conditions. The reaction mixture was concentrated invacuo. Water (2 mL) was added and stirred for 5 minutes. The solid was collected as the crude product which was purified by column chromatography on the Isco system to yield152G (25 mg, 65% yield). MS(ESI) m/z 435.2 (M+H)., 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; BRISTOL-MYERS SQUIBB COMPANY; HART, Amy C.; PITTS, William J.; MASTALERZ, Harold; GUO, Junqing; BROWN, Gregory D.; (148 pag.)WO2016/100166; (2016); 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 1.07 g (1.90 mmol) of the compound from Example 8A in 20 ml of DMF under argon were added 256 mg (2.28 mmol) of potassium tert-butoxide. After stirring at RT for 5 min, 408 mg (2.28 mmol) of 4-(bromomethyl)tetrahydropyran were added, and the mixture was stirred at bath temperature 100C. for 2 h. Subsequently, a further 136 mg (0.76 mmol) of 4-(bromomethyl)-tetrahydropyran were added and the mixture was stirred at bath temperature 100C. for another 2 h. After cooling to RT, the mixture was combined with the reaction mixtures from two similarly conducted prior experiments (batch size in each case 47 mg (0.08 mmol) of the compound from Example 8A). After removing the DMF, 60 ml of water and 60 ml of ethyl acetate were added to this combined mixture. After the phases had been separated, the aqueous phase was extracted once with 30 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated. The residue was taken up in a mixture of cyclohexane and ethyl acetate (9:1) and purified by means of column chromatography (120 g of silica gel, eluent: cyclohexane/ethyl acetate 9:1). 590 mg (47% of theory, purity 100%) of the title compound were obtained. [0384] 1H NMR (400 MHz, CDCl3): delta [ppm]=8.66 (s, 1H), 8.28 (d, 1H), 8.14 (dd, 1H), 7.95 (d, 2H), 6.92 (d, 2H), 4.78-4.62 (m, 2H), 4.21-4.13 (m, 1H), 4.03 (dd, 2H), 3.89-3.81 (m, 4H), 3.50-3.40 (m, 3H), 3.07-2.93 (m, 1H), 2.19-2.03 (m, 2H), 2.03-1.87 (m, 2H), 1.76 (dd, 2H), 1.72-1.61 (m, 1H), 1.47 (qd, 2H), 0.63-0.53 (m, 2H), -0.09 (s, 9H). [0385] LC/MS (Methode 1, ESIpos): Rt=1.51 min, m/z=560 [M+H]+., 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; BAYER PHARMA AKTIENGESELLSCHAFT; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMANN, Andreas; BROHM, Dirk; JOeRISSEN, Hannah; BOGNER, Pamela; GERISCH, Michael; LANG, Dieter; (44 pag.)US2017/114049; (2017); 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,125552-89-8

A mixture of 1H-indazole-5-sulfonic acid (4-ethylphenyl)amide (1.30 g; 4.31 mmol), cesium carbonate (2.11 g; 6.47 mmol) and 4-(bromomethyl)tetrahydropyran (680 mul; 5.18 mmol; 1.20 eq.) in N-methyl-2-pyrrolidone (10 ml) is stirred for 16 hours at a temperature of 50 C. The reaction medium is diluted with ethyl acetate (30 ml). The organic phase is washed with saturated NH4Cl solution (20 ml), with saturated NaHCO3 solution (20 ml) and with water (20 ml). The organic phase is dried (MgSO4), filtered and concentrated. The crude product is purified by preparative HPLC (C18 column, eluent: acetonitrile in water/0.1% of formic acid). The 1-(tetrahydropyran-4-ylmethyl)-1H-indazole-5-sulfonic acid (4-ethylphenyl)(tetrahydropyran-4-ylmethyl)amide (360 mg; 17%) is obtained in the form of a white solid. 1H NMR (DMSO-d6) delta: 1.08-1.23 (m, 5H), 1.25-1.47 (m, 5H), 1.52-1.62 (m, 2H), 2.60 (q, J=7.5 Hz, 2H), 3.13 (td, J=11.6, 2.2 Hz, 2H), 3.23 (td, J=11.3, 3.0 Hz, 2H), 3.43 (d, J=7.2 Hz, 2H), 3.72-3.87 (m, 4H), 4.38 (d, J=7.1 Hz, 2H), 6.97 (d, J=8.4 Hz, 2H), 7.17 (d, J=8.4 Hz, 2H), 7.46 (dd, J=9.0, 1.7 Hz, 1H), 7.84-7.98 (m, 1H), 8.10 (d, J=1.7 Hz, 1H), 8.29 (d, J=0.9 Hz, 1H). MS: [M+H]=498

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.

General procedure: To a stirred solution of 1H-indole-5-carbonitrile (1.5 g, 10.56 mmol) in DMF (8 mL) were added KI (1.75 g, 10.56 mmol) followed by NaH (1.26 g, 31.68 mmol) in portion wise at 0 C and reaction mixture was stirred at the same temperature for 5 mm. After 5 mi 4-(bromomethyl) tetrahydro-2H-pyran (2.1 mL, 15.84 mmol) was added to reaction mixture at 0 C then stirred atrt for 4 h. Progress of the reaction was monitored by TLC. Reaction mixture was quenched withcrushed ice, stirred for 15 mm, solid obtained in the reaction mixture was filtered off, dried undervaccum to get the pale cream solid (yield: 2.25g, 88.9 %).1H NMR (400 IVIFIz, CDC13) 8.0 (s, 1H), 7.47-7.36 (m, 2H), 7.18 (d, J= 3.14 Hz, 1H), 6.58 (d, J= 3.0 Hz, 1H), 4.02 (d, J 7.29 Hz, 2H), 3.98 (d, J= 3.38 Hz, 2H), 3.38-3.28 (m, 2H), 2.10-2.05(m, 1H), 1.5 1-1.40 (m, 4H),LC-MS m/z (M): calculated 240; found (M+H): 241, 125552-89-8

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

Reference£º
Patent; BIOIMICS AB; KIRSEBOM, Lars; UPADHAYAYA, Ram Shankar; KETHIRI, Raghava Reddy; VIRTANEN, Anders; (241 pag.)WO2019/88910; (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.

2-({[2-(4-Bromo-2-hydroxyphenyl)ethyl]sulfonyl}amino)-/V-tert-butylbenzenesulfonamide (3.2 g, 6.51 mmol) and 4-(bromomethyl)tetrahydro-2/-/-pyran (3.50 g, 19.54 mmol) were added to a solution of cesium carbonate (6.36 g, 19.54 mmol) in THF (10 mL) and the reaction mixture was heated using MW at 110 C, for 2 h. The reaction mixture was diluted with NH4CI (aq) and extracted with EtOAc two times, washed with water and concentrated. Purification by chromatography on silica using gradient elution of 0-50% EtOAc in n-heptane gave 3.0 g (78 % yield) of the title compound. XH NMR (500 MHz, DMSO-c/6) delta ppm 1.06 – 1.10 (m, 9 H) 1.17 – 1.27 (m, 2 H) 1.53 (br. s., 2 H) 1.81 – 1.92 (m, 1 H) 2.91 – 2.98 (m, 2 H) 3.25 (d, 7=1.58 Hz, 2 H) 3.45 – 3.54 (m, 2 H) 3.77 – 3.85 (m, 4 H) 7.05 (d, 7=1.58 Hz, 1 H) 7.10 – 7.14 (m, 3 H) 7.32 (s, 1 H) 7.59 – 7.70 (m, 3 H) 7.89 (dd, 7=8.04, 1.10 Hz, 1 H) 8.01 (s, 1 H) 8.77 (s, 1 H); MS m/z 589, 590 [M-H]”., 125552-89-8

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

Reference£º
Patent; ACTURUM LIFE SCIENCE AB; SOeDERMAN, Peter; SVENSSON, Mats A; KERS, Annika; OeHBERG, Liselott; HOeGDIN, Katharina; HETTMAN, Andreas; HALLBERG, Jesper; EK, Maria; BYLUND, Johan; NORD, Johan; (0 pag.)WO2016/85392; (2016); 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 methyl(R)-7-(7-chloro-10-(3-(4-chloro-3,5-dimethy lphenoxy)propy 1)-6-(3,5-dimethy 1-1H-pyrazol-4-y 1)-4-methy l-l-oxo-3,4-dihydropyrazino[1,2-a]indol-2(1H)-yl)-l-methyl-1H-indole-3-carboxylate(20 mg,0. 028mmol) in DMF(0.5 mL) was added NaH(1.4 mg,0.034 mmol) and stirred for 15 min at RT.4-(Bromomethyl)tetrahydro-2H-pyran(5.5 mg,0.031 mmol) was added,and the resultingmixure was stirred overnight then concentrated in vacuo. The residue was purified by flashchromatography(Combi-flash Rf,Hex/EtOAc = 0-70% gradient) to give the title compound(20 mg,88%) as white foam LCMS: RT = 2.107 min,MS(ES) 810.3(M+H).

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

Reference£º
Patent; VANDERBILT UNIVERSITY; LEE, Taekyu; TARR, James, C.; JEON, Kyuok; SALOVICH, James, M.; SHAW, Subrata; VEERASAMY, Nagarathanam; KIM, Kwangho; CHRISTOV, Plamen, P.; OLEJNICZAK, Edward, T.; ZHAO, Bin; FESIK, Stephen, W.; BIAN, Zhiguo; (526 pag.)WO2017/152076; (2017); 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

A mixture of 1H-indazole-5-sulfonic acid (2-chloromethyl-3-hydroxypropyl)(4-ethylphenyl)amide (1.26 g; 0.64 mmol), cesium carbonate (0.31 mg; 0.96 mmol) and 4-(bromomethyl)tetrahydropyran (100 mul; 0.76 mmol) in N-methyl-2-pyrrolidone (4 ml) is stirred for 1 hour at a temperature of 80 C. The reaction medium is diluted with ethyl acetate (20 ml). The organic phase is washed with saturated NH4Cl solution, with saturated NaHCO3 solution and with water. The organic phase is dried (MgSO4), filtered and concentrated. The crude product is purified by preparative HPLC (C18 column, eluent: acetonitrile in water/0.1% of formic acid). The 1-(tetrahydropyran-4-ylmethyl)-1H-indazole-5-sulfonic acid (3-chloro-2-hydroxymethylpropyl)(4-ethylphenyl)amide (100 mg; 31%) is obtained in the form of a colorless oil. 1H NMR (DMSO-d6) delta: 1.18 (t, J=7.6 Hz, 3H), 1.25-1.43 (m, 4H), 1.73 (p, J=6.4 Hz, 1H), 2.61 (q, J=7.6 Hz, 2H), 3.23 (td, J=11.3, 3.0 Hz, 2H), 3.35-3.41 (m, 1H), 3.46-3.52 (m, 1H), 3.52-3.63 (m, 2H), 3.69 (qd, J=10.8, 4.9 Hz, 2H), 3.82 (ddd, J=11.4, 4.3, 2.2 Hz, 2H), 4.39 (d, J=7.0 Hz, 2H), 4.69 (t, J=5.1 Hz, 1H), 6.95-7.02 (m, 2H), 7.16-7.22 (m, 2H), 7.44 (dd, J=9.0, 1.8 Hz, 1H), 7.92 (d, J=8.9 Hz, 1H), 8.10 (d, J=1.6 Hz, 1H), 8.31 (s, 1H). MS: [M+H]=506, 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; 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.

5-Bromo-2-oxo-1,2-dihydropyridine-3-carboxylic acid methyl ester (2.3 g, 10 mmol, 1.0 eq) was dissolved in DMF (30 mL), and 4- (bromomethyl) tetramethyl was added Hydrogen-2H-pyran (2.15 g, 12 mmol, 1.2 eq) and potassium carbonate (4.15 g, 30 mmol, 3.0 eq). The mixture was heated to 60 C and stirred for 4 hours. After the reaction was detected by LC-MS and TLC, the temperature was lowered to room temperature, suction filtered, the mother liquor was poured into water (50 mL), and EA (50 mL ¡Á 3) was extracted. The organic phases were combined, washed with saturated brine 3 times, dried, filtered, and concentrated. The crude product was purified by silica gel column chromatography (100-200 mesh silica gel, PE / EA = 0-50%) to obtain an off-white solid (1.8 g, yield: 55%).

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; 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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

To a vial charged with 2A (0.624 g, 1.591 mmol) and 4-(bromomethyl)tetrahydropyran (0.427 g, 2.386 mmol) in DMF (3.98 ml) was added cesium carbonate (1.555 g, 4.77 mmol). The vial was capped and stirred at 75 C ON. The reaction mixture was poured into a separatoryfunnel containing water and ethyl acetate. The aqueous layer was extracted with ethylacetate (3 x). The combined organics were washed with 10% lithium chloride solution (4x), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The cmderesidue was purified by column chromatography on the Isco system (80 g, 0 – 10%MeOH/CH2C12) providing 5A (0.3973 g, 0.810 mmol, 50.9% yield). MS(ESI) m/z 490.3(M+H)., 125552-89-8

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; HART, Amy C.; PITTS, William J.; MASTALERZ, Harold; GUO, Junqing; BROWN, Gregory D.; (148 pag.)WO2016/100166; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics