Category: 33821-94-2

33821-94-2, 2-(3-Bromopropoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,33821-94-2

Tetraethyl 4-(2-Tetrahydro-2H-pyranyloxy)butylene-1,1-bisphosphonate (31): To a suspension of NaH (60% suspension in mineral oil, 900 mg, 22.0 mmol) in dry THF (20 mL) was added dropwise tetraethyl methylenebisphosphonate (6.46 g, 22.4 mmol). The resulting clear solution was stirred 15 min at room temperature, after which 2-(3-bromopropoxy)tetrahydro-2H-pyran (5.05 g, 22.6 mmol) was added dropwise. The reaction mixture was heated to reflux for 6 h, diluted with CH2Cl2 (75 mL) and washed with brine (2*50 mL), dried (MgSO4) and evaporated. It was used as such in the following step.

33821-94-2 2-(3-Bromopropoxy)tetrahydro-2H-pyran 2777988, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; TARGANTA THERAPEUTICS, INC.; US2011/263534; (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.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

To a mixture of 4-iodo-lH-pyrazole (2.0 g, 10.3 mmol) and Cs2CO3 (5.04 g, 15.5 mmol) in MeCN (28 mL) was added 2-(3- bromopropoxy)tetrahydro-2H-pyran (1.84 mL, 10.8 mmol) and the mixture stirred at T overnight. The crude reaction mixture was poured into water and extracted with EtOAc (x 3). The combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by FCC, using a gradient of 0-80% EtOAc in cyclohexane, to give the title compound (2.95 g, 81%). NMR (300 MHz, CDC13): 150- 1.58 (4H, m), 1.65-1.90 (2H, m), 2.12 (2H, qn, J = 6.4 Hz), 3.35 (1H, dt, J = 10.2, 5.9 Hz), 3.46-3.54 (1H, m), 3.73 (1H, dt, J = 10.2, 5.9 Hz), 3.80-3.88 (1H, m), 4.26 (2H, td, J = 6.9, 1.5 Hz), 4.54 (1H, dd, J = 4.5, 3.1 Hz), 7.46 (1H, s), 7.50 (1H, s)., 33821-94-2

As the paragraph descriping shows that 33821-94-2 is playing an increasingly important role.

Reference£º
Patent; CHIESI FARMACEUTICI S.P.A.; ALCARAZ, Lilian; PANCHAL, Terry Aaron; JENNINGS, Andrew Stephen Robert; CRIDLAND, Andrew Peter; HURLEY, Christopher; WO2014/194956; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

33821-94-2, 2-(3-Bromopropoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 5-[(4-chlorophenyl)methyl]-4-[3-(trifluoromethoxy)phenoxy]-1,3,5,8-tetraazatricyclo[8.3.0.0^[2,6]]trideca-2(6),3-diene-7,9-dione(150 mg, 300 mmol, 1 equiv.), 2-(3-bromopropoxy)oxane (198.1 mg, 890 mmol, 3.000 equiv.) and K2CO3 (122.7 mg, 0.89 mmol, 3.0 equiv.) in DMF (15.0 mL) was stirred at 50 C for 16 hours. The reaction was cooled to room temperature and added EtOAc (100 mL) and H2O (100 mL). The organic layer was washed with brine (2×30 mL) and concentrated under reduced pressure which was purified by reverse phase flash with the following conditions (Column: Spherical C18 Column, 20-40um, 120 g; Mobile Phase A: Water (0.1% HOAc), Mobile Phase B: ACN; Flow rate: 60 mL/min; Gradient: 90% B to 98% B in 10 min, 254 nm) to afford 5-[(4-chlorophenyl)methyl]-8-[3-(oxan-2-yloxy)propyl]-4-[3-(trifluoromethoxy)phenoxy]-1,3,5,8-tetraazatricyclo[8.3.0.0^[2,6]]trideca-2(6),3-diene-7,9-dione (185 mg, 96.31%) as a light yellow oil.1H NMR (400 MHz, Chloroform-d) delta 7.43 (t, J = 8.3 Hz, 1H), 7.30 (s, 4H), 7.27 – 7.19 (m, 2H), 7.13 (d, J = 8.3 Hz, 1H), 5.73 (d, J = 14.9 Hz, 1H), 5.43 (d, J = 15.1 Hz, 1H), 4.65 – 4.49 (m, 1H), 4.15 (ddt, J = 19.0, 13.7, 7.1 Hz, 1H), 3.98 -3.61 (m, 4H), 3.46 (tt, J = 16.5, 7.6 Hz, 4H), 2.85 (dt, J = 12.2, 6.3 Hz, 1H), 2.18 – 2.02 (m, 2H), 1.99 – 1.77 (m, 3H), 1.76 – 1.48 (m, 6H)., 33821-94-2

The synthetic route of 33821-94-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GOLDFINCH BIO, INC.; DANIELS, Matthew, H.; YU, Maolin; HARMANGE, Jean-Christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; CASTLE, Neil, A.; MALOJCIC, Goran; (0 pag.)WO2019/173327; (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.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

Example 11; N-Cyclopropyl-3-[N-(2,2-dimethyl-1-oxoindan-5-yl)-N-(3-hydroxypropyl)amino]-4-methylbenzamidea) N-Cyclopropyl-3-[N-(2,2-dimethyl-1-oxoindan-5-yl)-N-(3-(tetrahydropyran-2-yloxy)propyl)amino]-4-methylbenzamideTo a suspension of N-cyclopropyl-3-(2,2-dimethyl-1-oxoindan-5-ylamino)-4-methylbenzamide (0.2 g, 0.57 mmol, obtained in example 2) in dry toluene (6.5 mL), sodium hydride (50 mg, 60% dispersion in oil, 1.14 mmol) and 15-crown-5 (4 mg, 0.02 mmol) were added under argon and the mixture was stirred at room temperature for 20 min. Then, 3-bromopropanol tetrahydropyranyl ether (0.13 g, 0.57 mmol) was added and the mixture was heated at 90 C. overnight. It was allowed to cool and diluted with EtOAc and saturated NaHCO3. The phases were separated and the organic phase was dried over Na2SO4. The solvent was evaporated to afford the desired compound (quantitative yield).LC-MS (method 1): tR=9.74 min; m/z=491.2 [M+H]+.

33821-94-2, The synthetic route of 33821-94-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PALAU PHARMA, S.A.; US2010/222363; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

33821-94-2, 2-(3-Bromopropoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 10; 6-[Lambda/-(2,4-Difluorophenyl)-Lambda/-(3-hydroxypropyl)amino]-2,2-dimethyl-1, 2,3,4- tetrahydronaphthalen-1 -one; a) 6-[Lambda/-(2,4-Difluorophenyl)-W-(3-(tetrahydropyran-2-yloxy)propyl)amino]- 2,2-dimethy 1-1 ,2,3,4-tetrahydronaphthalen-1 -one; To a suspension of 6-(2,4-difluorophenylamino)-2,2-dimethyl-1 , 2,3,4- tetrahydronaphthalen-1-one (1.94 g, 6.44 mmol, obtained in example 4) in dry toluene (70 mL), sodium hydride (0.56 g, 55% dispersion in oil, 12.83 mmol) and 15-crown-5 (47 mg, 0.21 mmol) were added under argon and the mixture was stirred at room temperature for 20 min. Then, 3-bromopropanol tetrahydropyranyl EPO ether (1.44 g, 6.44 mmol) was added and the mixture was heated at 90 0C for 4 h. It was allowed to cool and diluted with EtOAc and saturated NaHCO3. The phases were separated and the aqueous phase was reextracted with EtOAc. The combined organic phases were dried over Na2SO4 and the solvent was evaporated to afford the desired compound (quantitative yield). LC-MS (method 1): tR = 11.98 min; m/z = 444.2 [M+H]+., 33821-94-2

33821-94-2 2-(3-Bromopropoxy)tetrahydro-2H-pyran 2777988, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; J. URIACH Y COMPANIA S.A.; WO2007/337; (2007); 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.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

To a mixed solution of 62 (7.25 g, 32.5 mmol) and L12CUCI4 (16.2 mL, 0.1 M solution in THF, 1.62 mmol, 5 mol %) in THF (50 mL) at 0C was slowly added Grignard reagent ((cyclobutylmethyl)magnesium bromide) that5 was made from (bromomethyl)cyclobutane (9.69 g, 65.0 mmol) and grinded magnesium turnings (3.16 g, 130 mmol) in Et20 (50 mL). After the addition completed, stirred at 0C for 30 min and then at RT for 18 hr. The reaction was quenched by NH4Cl at 0C and stirred at RT for 20 min. Then the mixture was treated with hexanes and water. Organic phase was washed by brine, dried over Na2S04, and concentrated to give 63 (6.9 g, 100%) as a colorless oil. ‘H NMR (400 MHz, Chloroform-ri) d 4.57 (dd, J= 4.5, 2.7 Hz, 1H), 3.87 (ddd, .7= 11.1, 7.4, 3.4 Hz, 1H), 3.72 (dt, J = 9.6, 6.9 Hz, 1H), 3.56 – 3.45 (m, 1H), 3.37 (dt, J= 9.6, 6.7 Hz, 1H), 2.24 (dq, J= 15.5, 7.8 Hz, 1H), 2.10 – 1.93 (m,3H), 1.91 – 1.64 (m, 4H), 1.62 – 1.45 (m, 7H), 1.39 (q, J= 7.4 Hz, 2H), 1.25 (tdd, J= 10.0, 7.2, 3.9 Hz, 2H). 13C NMR (101 MHz, Chloroform-ri) d 98.78, 67.65, 62.28,36.79, 36.06, 30.73, 29.70, 28.32 (2C), 25.46, 23.77, 19.66, 18.43.

33821-94-2, 33821-94-2 2-(3-Bromopropoxy)tetrahydro-2H-pyran 2777988, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; TSRL, INC.; LIPKA, Elke D.; SIMON, Eric; WHITE, Andy, D.; HUTCHINGS, Kim, M.; GAN, Xinmin; (0 pag.)WO2020/6050; (2020); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

33821-94-2, 2-(3-Bromopropoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 5 7-benzyl-8-chloro-l-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-lH-purine-2,6(3H,7H)-dione To a solution of 7-benzyl-8-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-lH-purine-2,6(3H,7H)- dione (5 g, 12.32 mmol) in DMF (30 mL) was added 2-(3-bromopropoxy)tetrahydro-2H-pyran (3.60 g, 16.22 mmol, intermediate 14 step 1), followed by potassium carbonate (3.4 g, 24.64 mmol). The mixture was stirred at 65 C overnight. The mixture was diluted with ethyl acetate and water, and the phases were separated. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give 7-benzyl-8-chloro-l -(3-(tetrahydro-2FI-pyran-2- yloxy)propyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-lH-purine-2,6(3H,7H)-dione (6.3 g, 93.3% yield) as yellow oil. LCMS retention time 3.574 min; LCMS MNa+ 571 .

33821-94-2, 33821-94-2 2-(3-Bromopropoxy)tetrahydro-2H-pyran 2777988, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; HYDRA BIOSCIENCES, INC.; CHENARD, Bertrand; GALLASCHUN, Randall; WO2014/143799; (2014); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

33821-94-2, 2-(3-Bromopropoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a flask containing (S)-(but-3-yn-2-yloxy)(tert-butyl)dimethylsilane 34 (2.21 g, 12 mmol) in dry THF (40 mL) was added dropwise at -30 C a solution of n-BuLi (1.6 M in hexanes, 7.5 mL, 12 mmol) and the mixture was stirred for 30 min. The reaction mixture was cooled to -78 C, dry HMPA (5 mL) was added and the solution stirred for 15 min. Then a solution of 2-(3-bromopropoxy)tetrahydro-2H-pyran (2.54 g, 11.4 mmol) in dry THF (10 mL) was added dropwise and the reaction mixture was allowed to warm to 23 C slowly. After 40 h, the reaction mixture was diluted with water (5 mL) and extracted with Et2O (4 ¡Á 25 mL). The combined organic extracts were washed with H2O (5 mL) and brine (5 mL), dried over MgSO4, filtered and the solvents removed under reduced pressure. The crude product was purified by column chromatography (pentane:Et2O 90:10) to give 35 (3.02 g, 81% yield). 1H NMR (400 MHz, 21 C, CDCl3): 4.61-4.56 (m, 1H), 4.54-4.45 (m, 1H), 3.92-3.76 (m, 2H), 3.55-3.41 (m, 2H), 2.36-2.24 (m, 2H), 1.88-1.66 (m, 4H), 1.64-1.46 (m, 4H), 1.37 (d, J 6.4, 3H), 0.90 (s, 9H), 0.11 (d, J 3.9, 6H)., 33821-94-2

The synthetic route of 33821-94-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Krief, Alain; Wouters, Johan; Norberg, Bernadette; Kremer, Adrian; Arkivoc; vol. 2018; 5; (2018); p. 308 – 333;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

33821-94-2, 2-(3-Bromopropoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of 4-iodo-1H-pyrazole (2.0 g, 10.3 mmol) and Cs CO(5.04 g, 15.5 mmol) in MeCN (28 mL) was added 2-(3-bromopropoxy)tetrahydro-2H-pyran ( 1.84 mL, 10.8 mmol) and the mixturestirred at T overnight. The crude reaction mixture was poured into water andextracted with EtOAc (x 3). The combined organic layers were washed withbrine, dried (MgSO4) and concentrated in vacuo. The resulting residue waspurified by FCC, using a gradient of 0-80% EtOAc in cyclohexane, to give thetitle compound (2.95 g, 81%)., 33821-94-2

The synthetic route of 33821-94-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CHIESI FARMACEUTICI S.P.A.; Alcaraz, Lilian; Panchal, Terry Aaron; Jennings, Andrew Stephen Robert; Cridland, Andrew Peter; Hurley, Christopher; (80 pag.)KR2016/16973; (2016); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics