Tag: 19311-37-6

19311-37-6, 3-Bromotetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tert-butyl (6S)-3-hydroxy-6-methyl-6,7-dihydro-4H-pyrazolo[l,5- a]pyrazine-5-carboxylate (compound 3f, 70.0 mg, 0.277 mmol) and 3-bromotetrahedronfuran (62.7 mg, 0.415 mmol) in DMF (4.0 ml) was added NaH (16.6 mg, 0.415 mmol) at room temperature. The reaction mixture was stirred at room temperature for 3 h, then quenched with water (5.0 mL), diluted with EtOAc (60 mL). The organic layer was washed with water and brine, dried over Na2S04 and concentrated. The residue was purified by column chromatography (eluted with PE:EA = 10: 1-1: 1) to afford compound 3g (50.0 mg) as a yellow oil. LCMS (M+H+): 324., 19311-37-6

As the paragraph descriping shows that 19311-37-6 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HU, Taishan; LIU, Haixia; (78 pag.)WO2017/198744; (2017); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19311-37-6,3-Bromotetrahydrofuran,as a common compound, the synthetic route is as follows.

Example 204 1-(4-fluoro-3,5-dimethylbenzyl)-6-methyl-2-(piperazin-1-yl)-4-((tetrahydrofuran-3-yl)oxy)-1H-benzo[d]imidazole tert-Butyl 4-(4-bromo-1-(4-fluoro-3,5-dimethylbenzyl)-6-methyl-1H-benzo[d]imidazol-2-yl)piperazine-1-carboxylate (100 mg, 0.19 mmol, 1.00 eq), potassium hydroxide (21 mg, 0.38 mmol, 2.00 eq), tris(dibenzylideneacetone)dipalladium(0) (7 mg, 0.015 mmol Pd, 0.08 eq Pd), and 2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropyl-1,1′-biphenyl (Me4-t-BuXPhos) (14 mg, 0.030 mmol, 0.16 eq) were weighed into a vial. The vial was sealed, evacuated, and refilled with argon. The evacuation/refill process was repeated two additional times. A solution of 1,4-dioxane/water (1:1 v/v) (0.4 mL)-which had been degassed using three evacuation/refill cycles-was added. The vial was then heated to 90 C. and the progress of the reaction was monitored by LCMS. When the starting material had been completely consumed, the reaction mixture was allowed to cool to room temperature. Potassium hydroxide (21 mg, 0.38 mmol, 2.00 eq), hexadecyltrimethylammonium bromide (7 mg, 0.02 mmol), and 3-bromotetrahydrofuran (57 mg, 0.38 mmol) were added. The vial was then heated to 100 C. and the progress of the reaction was monitored by LCMS. When the intermediate tert-butyl 4-(1-(4-fluoro-3,5-dimethylbenzyl)-4-hydroxy-6-methyl-1H-benzo[d]imidazol-2-yl)piperazine-1-carboxylate had been completely consumed, the reaction mixture was allowed to cool to room temperature. CH2Cl2 (5 mL) and saturated aqueous NH4Cl (5 mL) were added. The resulting biphasic mixture was stirred for ten min before being passed through a phase separator. To the filtrate thus obtained was added trifluoroacetic acid (1 mL). The resulting solution was stirred at room temperature and the progress of the reaction was monitored by LCMS. When the intermediate tert-butyl 4-(1-(4-fluoro-3,5-dimethylbenzyl)-6-methyl-4-((tetrahydrofuran-3-yl)oxy)-1H-benzo[d]imidazol-2-yl)piperazine-1-carboxylate had been completely consumed, the reaction mixture was concentrated in vacuo. The residual oil was purified by reverse phase preparative HPLC. The title compound was obtained as a white solid as its corresponding trifluoroacetate salt (30 mg, 29% yield). 1H NMR (400 MHz, CD3OD) delta 6.93 (s, 1H), 6.92 (s, 1H), 6.78 (2s ovlp, 2H), 5.34 (s, 2H), 5.29 (m, 1H), 4.05 (m, 3H), 3.91 (td, J=8.3, 4.6 Hz, 1H), 3.64 (m, 4H), 3.41 (m, 4H), 2.41 (s, 3H), 2.37 (m, 1H), 2.24 (m, 1H), 2.21 (2s ovlp, 6H). MS (ESI) (M+H+) m/z=439.30. LCMS Ret time (UV 214/254): 1.188 min.

19311-37-6, As the paragraph descriping shows that 19311-37-6 is playing an increasingly important role.

Reference£º
Patent; Vanderbilt University; Fesik, Steve; Waterson, Alex; Burns, Michael; Sun, Qi; Phan, Jason; Salovich, James M.; Abbott, Jason R.; Little, Andrew; (159 pag.)US10501421; (2019); B1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19311-37-6,3-Bromotetrahydrofuran,as a common compound, the synthetic route is as follows.

Step 1: Preparation of Compound 3 (0434) A mixture of tert-butyl N-hydroxy-N-methyl-carbamate (1.00 g, 6.79 mmol, 1.00 eq), 3-bromotetrahydrofuran (1.23 g, 8.15 mmol, 1.20 eq), Cs2CO3 (3.32 g, 10.18 mmol, 1.50 eq) in DMF (10.00 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 70 C. for 16 hour under N2 atmosphere. TLC showed the reaction was completed. The mixture was poured into water (20 mL) and stirred at 5 min. The aqueous phase was extracted with ethyl acetate (15 mL*2). The combined organic phase was washed with brine (20 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate=100/1 to 50/1) to give tert-butyl N-methyl-N-tetrahydrofuran-3-yloxy-carbamate (905.00 mg, 4.17 mmol, 61.35% yield) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 4.62-4.71 (m, 1H) 3.89-4.01 (m, 2H) 3.81-3.88 (m, 1H) 3.75 (dd, J=10.54, 4.39 Hz, 1H) 3.10 (s, 3H) 2.13 (dtdd, J=12.23, 5.32, 5.32, 2.54, 1.32 Hz, 1H) 1.92-2.05 (m, 1H) 1.47-1.53 (m, 9H).

19311-37-6, As the paragraph descriping shows that 19311-37-6 is playing an increasingly important role.

Reference£º
Patent; Novira Therapeutics, Inc.; Hartman, George D.; Kuduk, Scott; (45 pag.)US2016/185777; (2016); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19311-37-6,3-Bromotetrahydrofuran,as a common compound, the synthetic route is as follows.,19311-37-6

4,4?-Di-tert-butyl-2,2?-bipyridine (16.10 mg, 0.06 mmol, 0.6 equiv.) and 1,2-dimethoxyethane -dichloronickel (1:1) (10.99 mg, 0.05 mmol, 0.5 equiv.) were charged under argon in a flask and suspended in dry 1 ,2-dimethoxyethane (10 ml). This mixture was sonicated for 5 mm. In a separated microwave vial under argon Iridium( 1+), [4,4?-bis( 1,1 -dimethylethyl)-2,2?-bipyridine-icNl ,icNl ?]bis [3,5- difluoro-2- [5-(trifluoromethyl)-2-pyridinyl-icN]phenyl-icC] -, (OC-6-3 3)-, hexafluorophosphate( 1-) (1:1) (CAS 870987-63-6) (5.61 mg, 5.00 jimol), N-[5-(7-bromo-4-oxoquinazolin-3(4H)-yl)-2- (trifluoromethoxy)phenyl] -1 -(4-methylpiperazin- 1 -yl)cyclopropanecarboxamide (56.6 mg, 100 jimol),and lithium hydroxide (4.79 mg, 200 jimol) were charged in a 2 mL vial. 1 mL of the nickel pre-catalyst solution was syringed into the vial containing the reaction mixture. The solution was degassed a second time by sparging with argon while stirring for 10 minutes. Under a constant flow of argon, 3- bromotetrahydrofurane (racemate) (14 jil, 150 jimol) and 1,1,1,3,3,3-hexamethyl-2- (trimethylsilyl)trisilane (31 jil, 100 jimol) were added to the reaction mixture using a Hamilton syringe.The reaction mixture was iffadiated with one 34 W blue LED lamp in the EvoluChemTM PhotoChemistry Device using the 8 x 2 mL vial rack which contains an incorportated fan for cooling to maintain the experiment at room temperature. The reaction mixture was then allowed to stir in the device for 15 hours. The reaction mixture was charged completely on a silica gel column and a chromatographic separation was performed with a gradient of dichloromethane/methanol from 100:0 to90:10. The material obtained was purified by preparative RP-HPLC on a 125x30mm column with acetonitrile/water (0.2% ammonia) to provide 10.0 mg (96 % purity, 17 % yield) of the title compound.LC-MS (Method 2): R = 1.88 mm; MS (ESIpos): m/z = 558 [M+H]1HNMR (500 MHz, DMSO-d6) [ppm]: -0.007 (1.09), 0.007 (0.77), 1.106 (1.50), 1.115 (4.03), 1.122 (4.31), 1.129 (1.98), 1.237 (1.98), 1.245 (4.44), 1.251 (3.60), 1.261 (1.50), 1.908 (0.53), 1.968 (0.47),1.983 (1.12), 1.992 (0.62), 1.999 (1.14), 2.008 (1.32), 2.014 (0.54), 2.024 (1.29), 2.039 (0.54), 2.194(16.00), 2.359 (0.43), 2.362 (0.50), 2.366 (0.46), 2.375 (0.89), 2.384 (1.03), 2.391 (1.41), 2.400 (1.97),2.406 (1.52), 2.409 (1.46), 2.415 (2.29), 2.425 (2.09), 2.431 (2.27), 2.453 (4.01), 2.519 (0.66), 2.523(0.54), 3.249 (1.47), 3.265 (1.68), 3.286 (1.08), 3.577 (0.40), 3.592 (1.13), 3.607 (1.72), 3.622 (1.37),3.636 (0.55), 3.651 (2.79), 3.667 (2.88), 3.681 (1.82), 3.813 (1.07), 3.828 (2.52), 3.844 (2.88), 3.859(1.21), 3.981 (1.12), 3.990 (1.19), 3.997 (2.06), 4.007 (2.02), 4.014 (0.95), 4.023 (0.88), 4.079 (2.08),4.094 (2.64), 4.095 (2.57), 4.110 (1.82), 7.374 (2.49), 7.379 (2.51), 7.391 (2.59), 7.396 (2.80), 7.528(2.04), 7.531 (2.08), 7.545 (2.10), 7.548 (2.20), 7.629 (3.95), 7.633 (3.60), 7.677 (1.95), 7.680 (1.86),7.691 (0.78), 7.694 (1.63), 7.697 (1.50), 8.127 (4.08), 8.143 (3.73), 8.352 (9.84), 8.365 (0.76), 8.584(4.25), 8.589 (4.19), 10.650 (3.53).

The synthetic route of 19311-37-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; JIMENEZ, NUNEZ, Eloisa; BORISSOFF, Julian; HAHN, Michael; DIETZ, Lisa; ZDENKA, GAUGAZ, Fabienne; BENDER, Eckhard; LANG, Dieter; GIESE, Anja; THEDE, Kai; ZORN, Ludwig; BOULTADAKIS ARAPINIS, Melissa; (190 pag.)WO2019/63708; (2019); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19311-37-6,3-Bromotetrahydrofuran,as a common compound, the synthetic route is as follows.

[00494] To a solution of 119-1 (50 mg, 0.16 mmol, 1.00 eq) and 119-2 (32.2 mg, 0.21 mmol, 1.30 eq) in DMF (3 mL) was added K2C03 (45.3 mg, 0.33 mmol, 2.00 eq). The reaction was heated to 100C for 16 hr. LCMS showed that -80% of desired MS signal was detected. The reaction was diluted with EtOAc (20 mL) and washed with brine (2* 10 mL). The organic layer was dried over Na2S04 and concentrated. The crude product was purified by Prep.HPLC (acidic conditions) to give the title compound (17.36 mg, 46.25 umol, 28.24% yield). 1HNMR and LCMS confirmed that the desired product was obtained. LCMS (ESI): RT = 0.910 min, mass calc. for Ci8Hi6F3N50 375.13, m/z found 376.0[M+H]+; 1HNMR (400 MHz, CDC13) 9.05 (s, 1H), 8.21 (dd, J= 8.0, 1.6 Hz, 1H), 7.60 – 7.50 (m, 3H), 7.40 – 7.35 (m, 1H), 7.29 (d, J= 8.4 Hz, 2H), 7.05 (t, J= 8.0 Hz, 1H), 5.65- 5.50 (m, 1H), 4.40 – 4.25 (m, 3H), 4.15- 4.00 (m, 1H), 2.80 – 2.65 (m, 1H), 2.65- 2.50 (m, 1H).

19311-37-6 3-Bromotetrahydrofuran 12929516, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (396 pag.)WO2018/204532; (2018); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19311-37-6,3-Bromotetrahydrofuran,as a common compound, the synthetic route is as follows.

10560] 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 3-bromotetrahydrofuran (17.81 mg, 0.118 mmol) was added. The reaction was heated to 70 C. and stirred for 3 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 2.37a was used as is for the next step, assume quantitative yield. EC-MS (mlz): 452.4 [M+H], 0.75 mm.

As the paragraph descriping shows that 19311-37-6 is playing an increasingly important role.

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;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem