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

A 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 warmed with 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 min. 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 min, 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. ammonium chloride, 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. 1H NMR (400 MHz, CDCl3) delta 4.11 (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

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

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; (220 pag.)US2016/176864; (2016); 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 stirred solution of 2-chloro-N-i sopropyl -5 -(1 H-pyrazol-4-yl)pyridin-4-amine(200 mg, 0.845 mmol) in DMF (4 mL) was added Cs2CO3 (413 mg, 1.27 mmol) and 4-bromotetrahydro-2H-pyran (167 mg, 1.01 mmol). The reaction mixture was heated at160 C for 2.5 h under microwave irradiation. After cooling, the mixture wasconcentrated to dryness and then partitioned between EtOAc (150 mL) and ice water (20mL). The layers were separated and the organic layer washed again with cold water. Theorganic layer was dried over Na2SO4, filtered, and concentrated. The product was purified via column chromatography (30% EtOAc/pet ether) to afford 2-chloro-N- i sopropyl -5 -(1 -(tetrahydro-2H-pyran-4-yl)- 1 H-pyrazol-4-yl)pyridin-4-amine (80 mg, 30% yield). LCMS 321.1 (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; BRISTOL-MYERS SQUIBB COMPANY; DUNCIA, John V.; GARDNER, Daniel S.; HYNES, John; MACOR, John E.; SANTELLA, Joseph B.; WU, Hong; NAIR, Satheesh Kesavan; PAIDI, Venkatram Reddy; SARKUNAM, Kandhasamy; SISTLA, Ramesh Kumar; POLIMERA, Subba Rao; (72 pag.)WO2016/210037; (2016); 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

B. 3- [5-AMINO-4- (TETRAHYDRO-PYRAN-4-CARBONYL)-IMIDAZOL-1-YL]-N- CYCLOPROPYL-4-METHYL-BENZAMIDE A solution of 4-bromo-tetrahydro-pyran (0.82g, 5MMOL) in dry THF (IOML) was added dropwise to the suspension of magnesium (132mg, 5.5 mmol) and iodine (25mg) in dry THF (20 mL) at 50 C under N2. The mixture was stirred for 30 min after addition at 50 C, then cooled to room temperature. Then a THF (LOML) solution of 3- (5-AMINO-4-CYANO-IMIDAZOL-1-YL)-N-CYCLOPROPYL-4-METHYL-BENZAMIDE (90 mg, 0.32 mmol) was added to the reaction mixture and it was stirred at room temperature for 3h then quenched with HC1 (2N) and stirred at room temperature overnight. The pH of the solution was adjusted PH-8 with saturated aqueous K2CO3 was and it was extracted with EtOAc. The organic layer was washed by water and brine, dried over NA2SO4, and concentrated. The crude product was purified by column chromatography on silical gel (EtOAc-EtOAc : MeOH: Et3N = 100: 10: 1), and the product was obtained as a beige solid (35 mg, 30 %)., 25637-16-5

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

Reference£º
Patent; TRIAD THERAPEUCTICS, INC.; WO2005/9973; (2005); 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

A dry 50 mL flask was charged with magnesium (173 mg, 7.13 mmol) and a crystal of iodine. Under nitrogen, the solids were stirred vigorously while being warmed with 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 (0.530 mL, 4.76 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 min. After cooling to room temperature, the solution was transferred to a stirred solution of 2-cyclopropylacetaldehyde (400 mg, 2.38 mmol) in THF (4 mL) at -78 C. After stirring for 5 min, the ice bath was removed, and the reaction allowed to warm to room temperature. The reaction was placed in a 0 C. bath and quenched by the cautious addition of sat. aq. NH4Cl (4 mL). The reaction was diluted with EtOAc and poured into brine (10 mL). The layers were separated, and the aqueous was extracted with a second portion of EtOAc. The resulting organics were dried over magnesium sulfate, filtered, and concentrated to give product (410 mg, quant.) as near colorless oil, which was used without purification. 1H NMR (400 MHz, DMSO-d6) delta 4.03-4.0 (m, 2H), 3.54-3.35 (m, 3H), 1.51-1.34 (m, 4H), 0.8 (m, 1H), 0.59-0.46 (m, 2H), 0.19-0.05 (m, 2H)., 25637-16-5

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

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; (220 pag.)US2016/176864; (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 solution of Compound 141C (300 mg, 0.71 mmol) in dry THF (10 mL) was dropped a solution of phenylmagnesium bromide in THF (1 M, 1 mL, 1.0 mmol) at -78 over 5 minutes. The mixture was stirred at -78 for 1 hour. The reaction mixture was poured into saturated aqueous ammonium chloride solution (50 mL) and extracted with ethyl acetate (50 mL x 3). The combined organic layers was washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified with flash column chromatography on silica gel (ethyl acetate in petroleum, 20% v/v) to furnish Compound 141. LC-MS (ESI) m/z: 501 [M+H]+;1H-NMR (CDCl3, 400 MHz): delta (ppm) , 4.45 (s, 1H), 7.33-7.40 (m, 9 H), 7.45 (m, 2H), 7.59-7.61 (m, 2H).To a mixture of magnesium (159 mg, 6.6 mmol) and a small amount of iodine in anhydrous THF (10 mL) were added 1,2-dibromomethane (0.1 mL) and heated at 50 C for 10 minutes. To the mixture was dropped a solution of Compound 174A (1 g, 4.4 mmol) in THF (2 mL) and stirred at 80 C for 2 hours. The resulting Grignard reagent 174B was cooled down to room temperature and used directly in the next step.Compound 174 was synthesized by employing the procedure described for Compound 141 using Grignard reagent 174B in lieu of phenylmagnesium bromide. LC-MS (ESI) m/z: 1163 [2M+Na]+;1H-NMR (CDCl3, 400 MHz): delta (ppm) 1.64-1.71 (m, 1H), 1.82- 1.90 (m, 1H), 2.10-2.19 (m, 2H), 2.39-2.46 (m, 2H), 4.58-4.64 (m, 1H), 6.77 (d, J = 8.4 Hz, 2H), 7.27-7.29 (m, 2H), 7.30-7.34 (m, 4H), 7.37-7.38 (m, 2H), 7.56 (d, J = 8.0 Hz, 2H).Compounds 207B and 207 were synthesized by employing the procedures described for Compounds 174B and 141 using Compounds 207A, 207B, and at -60 C in lieu of Compounds 174A, phenylmagnesium bromide, and -78 C.Compound 207B as a Grignard reagent solution, which was directly used in the next step. Compound 207. LC-MS (ESI) m/z: 509 [M+H]+;1H-NMR (DMSO-d6, 400 MHz): delta (ppm) 1.02-1.12 (m, 1H), 1.54-1.65 (m, 2H), 1.75-1.86 (m, 1H), 1.94-2.01 (m, 1H), 304-3.18 (m, 2H), 3.77-3.86 (m, 2H), 3.39 (d, J = 8.4 Hz, 2H), 7.53 (d, J = 8.8 Hz, 2H), 7.68- 7.79 (m, 5H).

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

Reference£º
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; (552 pag.)WO2017/214505; (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.

Step 1: (5-Methyl-i ,2-oxazol-3-yl)(oxan-4-yl)methanol4-Bromooxane (270 jiL, 2.42 mmol) was added drop wise to a stirred suspension of magnesium (58.9 mg, 2.42 mmol) and one crystal of iodine in THF (1700 jiL) at ambient temperature. The reaction mixture was stirred for 1 h before 5-methyl-i ,2 – oxazole-3-carbaldehyde (119 jiL, i.28 mmol) was added in a single portion. The reaction mixture was then stirred for 16 h. The reaction mixture was quenched with a minimumamount of saturated aqueous ammonium chloride (5 mL), and the volatiles were removed under reduced pressure. The crude reaction material was purified using reverse phase preparatory HPLC (TFA/acetonitrile/water). (5-Methyl-i ,2 -oxazol-3 -yl)(oxan-4- yl)methanol (90.9 mg, 0.461 mmol, 36 %) was isolated as a colorless oil. LC/MS (M+H) = 198.2; LC/MS RT = 0.84 mm (Column: Phenomenex Luna 30 x 2.0 mm 3u; MobilePhase A: 10:90 acetonitrile:water with 0.1% TFA; Mobile Phase B: 90:10 acetonitrile:water with 0.1% TFA; Temperature: 40 C; Gradient: 0-100% B over 2 mm; Flow: 1 mL/min).

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

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

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

10565] To 2.lh (18 mg, 0.047 mmol) was added DMF (Volume: 0.5 mE) and cesium carbonate (53.8 mg, 0.165 mmol). The reaction was stirred at room temperature for 5 minutes then 4-bromotetrahydro-2H-pyran (19.47 mg, 0.118 mmol) was added. The reaction was heated to 70 C. and stirred for 20 hours or until done by ECMS. The reaction was cooled, 0.5 ml of DMF was added, then filtered through a 0.45 nM in line filtet The DMF solution with the desired product 2.38a was used as is for the next step, assume quantitative yield. EC-MS (mlz): 466.5 [M+H], 0.79 mm.

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

Reference£º
Patent; Novartis AG; FU, Jiping; HAN, Wooseok; KARUR, Subramanian; LU, Peichao; PFISTER, Keith Bruce; YOUNG, Joseph Michael; (97 pag.)US2018/312507; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics