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

The title compound was prepared following the procedure for Intermediate 28, starting from 4- (bromomethyl)tetrahydro-2f/-pyran (0.16 g, 0.89 mmol) and /V-tert-butyl-2-({[2-(4-chloro-2- hydroxyphenyl)ethyl]sulfonyl}amino)benzenesulfonamide (0.20 g, 0.45 mmol) with cesium carbonate (0.22 g, 0.67 mmol) in DMF (3 mL). Purification by chromatography on silica using gradient elution 16-50 % EtOAc in heptane gave 126.4 mg (52 % yield) of the title compound. 1H NMR (500 MHz, DMSO-d6) delta ppm 1.03 – 1.13 (m, 9 H) 1.17 – 1.32 (m, 2 H) 1.48 – 1.64 (m, 2 H) 1.79 – 1.94 (m, 1 H) 2.89 – 3.04 (m, 2 H) 3.25 (td, 2 H) 3.44 – 3.55 (m, 2 H) 3.75 – 3.87 (m, 4 H) 6.91 (dd, 1 H) 7.00 (d, 1 H) 7.17 (d, 1 H) 7.27 – 7.37 (m, 1 H) 7.58 – 7.70 (m, 2 H) 7.89 (dd, 1 H) 8.01 (s, 1 H) 8.77 (s, 1 H); MS (ES ) m/z 543, 545, 547 [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; 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

A mixture of 4-(bromomethyl)tetrahydropyran (1.0 g; 5.58 mmol) and sodium hydrogen sulfide (0.44 g; 7.82 mmol) in dimethylformamide (4 ml) is stirred at room temperature for 2 hours. The reaction medium is diluted with ether and acidified by addition of concentrated HCl and then extracted. The organic phases are combined, washed with water, dried over magnesium sulfate, filtered and concentrated to dryness. The bis[(tetrahydropyran-4-yl)methane bisulfide (565.00 mg; 77%) obtained in the form of a clear oil is used directly in the next reaction. (0559) MS: [M+H]=263, 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; BOUIX-PETER, Claire; OUVRY, Gilles; THOREAU, Etienne; (132 pag.)US2018/170869; (2018); 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.

The compound 3 (300 mg, 0 . 70 mmol, 1.0 eq), dissolved in DMF (3 ml), the compound is added under the room temperature condition 4 (150 mg, 0 . 84 mmol, 1.2 eq), K2CO3(200 Mg, 1 . 40 mmol, 2.0 eq), lidded cooking vessel 100 C reaction 4 hours. TLC plate display the reaction is complete, the crude product of job then turns on lathe, coils over post (PE:EA=4:1), to obtain compound EXP 3 (320 mg, yield: 78%).

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

Reference£º
Patent; Nanjing Kefeipingshenghui Pharmaceutical Co., Ltd.; Jin Qiu; Qin Yinlin; Su Mei; Qiu Yanan; Lou Yajing; (24 pag.)CN109111435; (2019); A;,
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 70(IS, 2R) and (IR, 2S)-2-(4-chlorophenyl)-l’-((tetrahydro-2H-pyran-4-yl)spiro[cyclopropane-l,3′-indolin]-2′-oneRacemic (I S, 2R)-2-(4-chlorophenyl)spiro[cyclopropane-l,3′-indolin]-2′-one and (1R, 2S)- 2-(4-chlorophenyl)spiro[cyclopropane-l,3′-indolin]-2′-one (270 mg, 1.0 mmol, 1.0 equiv.) were added to a stirred solution of sodium hydride (60 %, 60 mg, 1.5 mmol) in 5 mL of DMF under argon atmosphere at 0C. After stirring for 1 hour, 4-bromomethyl- tetrahydropyran (215 mg, 1.2 mmol) was added. The reaction mixture was stirred for 14 hours at room temperature. The crude product was purified by HPLC to give the title compound as a white solid (258 mg, 70 %). LC/MS m/e calcd. for C22H22CINO2: 367, observed (M+H)+: 368.2 1H MR (400 MHz, MeOD-d4) 5ppm 1.39 – 1.55 (m, 2 H) 1.65 (dd, J=13.14, 1.77 Hz, 2 H) 2.11 – 2.25 (m, 3 H) 3.22 (t, J=8.46 Hz, 1 H) 3.37 – 3.47 (m, 2 H) 3.79 (d, J=7.33 Hz, 2 H) 3.94 – 4.04 (m, 2 H) 6.09 (d, J=7.58 Hz, l H) 6.76 (t, J=7.58 Hz, 1 H) 7.11 (d, J=7.83 Hz, 1 H) 7.17 – 7.25 (m, 3 H) 7.33 (d, J=8.34 Hz, 2 H). MS calcd. For C22H22CINO2 367, obsd. (ESf) [(M+H)+] 368.

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

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Li; HUANG, Mengwei; FENG, Lichun; HE, Yun; YUN, Hongying; WO2011/69298; (2011); 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

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.

Intermediate 1 (5.1 g, 22.1 mmol), 4-(bromomethyl)tetrahydro-2H-pyran (4.35 g24.3 mmol) and caesium carbonate (36 g, 110 mmol) were stirred in DMF (150 mL)at 120C for 22h. The reaction mixture was filtered and the filtrate concentratedunder reduced pressure. Crude material (7.1 g) contained the title compoundalongside with the corresponding carboxylic acid.This mixture was stirred in methanol (150 mL) and acetyl chloride (4.23 g, 53.9 mmol) at 90C for 16 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. Crude material was purified by columnchromatography (silica gel, hexane/ EE gradient) to afford the title compound 6.02 g (83% yield).1H NMR (400 MHz, DMSO-d6) 6 [ppm] 1.26 – 1.39 (m, 2 H) 1.66 (dd, J=12.80, 1.90 Hz, 2 H) 1.94 – 2.06 (m, 1 H) 3.29 – 3.37 (m, 2 H) 3.85 – 3.90 (m, 5 H) 3.92 (d, J=6.34 Hz, 2 H) 7.42 (dd, J=2.41, 1.39 Hz, 1 H) 7.46 (t, J=2.15 Hz, 1 H) 7.62 (t,J=1.52 Hz, 1 H).

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

Reference£º
Patent; EVOTEC AG; DAVENPORT, Adam James; BRAEUER, Nico; FISCHER, Oliver Martin; ROTGERI, Andrea; ROTTMANN, Antje; NEAGOE, Ioana; NAGEL, Jens; GODINHO-COELHO, Anne-Marie; (703 pag.)WO2016/91776; (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

Add 4-oxo-5- (p-tolyl) -1,4-dihydropyridine-3-carboxylic acid ethyl ester (1.56 g, 6.1 mmol, 1.0 eq) to DMF (45 mL), and then add cesium carbonate (3.96g, 12.2mmol, 2.0eq)And 4- (bromomethyl) tetrahydro-2H-pyran (1.2 g, 6.7 mmol, 1.1 eq), heated to 100 C. and reacted overnight. After detecting the reaction by TLC and LC-MS, cool to room temperature, add water (100 mL), separate the layers, extract the aqueous phase with ethyl acetate (50 mL ¡Á 5), wash with saturated brine (50 mL ¡Á 3), dry, filter, and concentrate. The crude product was subjected to silica gel column chromatography to obtain a yellow solid (1.2 g, 77%).

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

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 4-(bromomethyl)tetrahydropyran (300.00 mg, 1.68 mmol, 1.00 eq) and potassium thioacetate (575.62 mg, 5.04 mmol, 3.00 eq) were dissolved in DMF (10.00 mL). The resulting mixture was then stirred at 25 C for 3 h under N2 atmosphere. The reacting solution was quenched with sat. aq. NaHC03 solution (50 mL) and extracted with DCM (50 mL x 3). The combined organic layers were concentrated under reduced pressure to afford S- (tetrahydropyran-4-ylmethyl) ethanethioate (245.00 mg, 1.41 mmol, 83.69% yield) as black brown oil. The product was confirmed by LC-MS and used directly for the next step without further purification., 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; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (94 pag.)WO2017/132474; (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

To a solution of 3,5-dichloro-4-((l,4-dimethyl-6-(trifluoromethyl)-lH-indol-2-yl)methyl)pyridin-2-ol (200 mg, 0.514 mmol) in DMF (2.6 ml) was added potassium carbonate (284 mg, 2.056 mmol) and 4- (bromomethyl)tetrahydropyran (0.135 ml, 1.028 mmol) and reaction mixture was stirred at 100C for 2 hours. The reaction mixture was diluted with water and the obtained aqueous layer was extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with 5-100% ethyl acetate in dichloromethane) then by preparative LCMS to give 2-((3,5- dicMoro-2-((tetrahydro-2H-pyran-4-yl)methoxy)pyridin-4-yl)methyl)-l,4-dimethyl-6- (trifluoromethyl)-lH-indole (108 mg, 40%) as a white solid LC/MS (Method g) Rt = 2.26 min.; MS m/z: 487 [M+H]+ NMR (DMSO-d6, 400MHz): delta 8.32 (m, 1H), 7.70 (s, 1H), 7.07 (s, 1H), 5.80 (s, 1H), 4.42 (s, 2H), 4.24 (d, J=6.3 Hz, 2H), 3.91 (s, 3H), 3.88 (m, 2H), 3.34 (m, 2H), 2.38 (s, 3H), 2.07 (m, 1H), 1.68 (m, 2H), 1.39 (m, 2H) and 3,5-dichloro-4-((l,4-dimethyl-6-(trifluoromethyl)-lH-indol-2-yl)methyl)-l- ((tetrahydro-2H-pyran-4-yl)methyl)pyridin-2(lH)-one (46 mg, 18%) as a white solid. LC/MS (Method g) R, = 1.84 min.; MS m/z: 487 [M+H]+ NMR (DMSO-d6, 400MHz): delta 8.14 (s, 1H), 7.69 (s, 1H), 7.07 (s, 1H), 6.00 (s, 1H), 4.30 (s, 2H), 3.82-3.95 (m, 7H), 3.20-3.30 (m, 2H), 2.41 (s, 3H), 2.09 (m, 1H), 1.48 (m, 2H), 1.30 (m, 2H).

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

Reference£º
Patent; ABBVIE INC.; ARGIRIADI, Maria A.; BREINLINGER, Eric; CUSACK, Kevin P.; HOBSON, Adrian, D.; POTIN, Dominique; BARTH, Martine; AMAUDRUT, Jerome; POUPARDIN, Olivia; MOUNIER, Laurent; KORT, Michael, E.; (392 pag.)WO2016/198908; (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,125552-89-8

To a stirred solution of Intermediate 3 (250 mg, 1 mmol) and 4-(bromomethyl)tetrahydro-2H-pyran (449 mg, 2.51 mmol) in anhydrous MeCN (7 mL)was added dipotassium carbonate (347 mg, 2.51 mmol). The reaction mixture wasstirred overnight at 100C, cooled to RT, filtered through Celite and concentrated under reduced pressure. The resulting material was purified by chromatography using si[ica ge[ (gradient: hexane/EE) to give 1.0 g (76 % yie[d) of the tit[e compound as a co[our[ess oi[.1H NMR (500MHz, CDC[3): 6 [ppm] 8.08 (t, J = 1.4 Hz, 1H), 7.69-7.67 (m, 1H), 7.57 (dd, J = 2.5, 1.4 Hz, 1H), 7.53 – 7.51 (m, 1H), 4.05 – 4.00 (m, 2H), 3.94 (s, 3H),3.92 (d, J = 6.5 Hz, 2H), 3.49 – 3.42 (m, 2H), 2.53 – 2.52 (m, 3H), 2.14 – 2.03 (m,1H), 1.80- 1.75 (m, 2H), 1.53- 1.43 (m, 2H).LCMS (Ana[ytica[ Method A) Rt = 1 .45 min, MS (ESipos): m/z = 348 (M+H).

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

Reference£º
Patent; EVOTEC AG; DAVENPORT, Adam James; BRAEUER, Nico; FISCHER, Oliver Martin; ROTGERI, Andrea; ROTTMANN, Antje; NEAGOE, Ioana; NAGEL, Jens; GODINHO-COELHO, Anne-Marie; (703 pag.)WO2016/91776; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics