Category: 5414-19-7

Electric Literature of 5414-19-7, The chemical industry reduces the impact on the environment during synthesis 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, I believe this compound will play a more active role in future production and life.

TP5 – To 200 mg (0.984 mmol) of (R)-6-(4-aminophenyl)-5-methyl-4,5- dihydropyridazin-3(2H)-one dissolved in 1 mL of DMF was added 250 (2.00 mmol) of bis (2-bromoethyl) ether and 400 mg of K2CO3 and the mixture was stirred overnight at 60 C. The next day another 250 mu^ of bis (2-bromoethyl) ether and 170 mg of K2CO3 was added. After 3 h, EtOAc and water were added, the water was rinsed with EtOAc, the combined EtOAc washes were dried and concentrated. Chromatography with 0-4% MeOH in CH2C12 yielded 125 mg of product (46%). XH NMR (300 MHz, CDC13) delta 8.61 (s, 1H), 7.68 (d, J= 8.8, 2H), 6.92 (d, J= 8.8, 2H), 3.99 – 3.76 (m, 4H), 3.44 – 3.31 (m, 1H), 3.29 – 3.22 (m, 4H), 2.70 (dd, J= 6.7, 16.8, 1H), 2.46 (d, J= 16.7, 1H), 1.24 (d, J= 7.3, 3H). 13C NMR (75 MHz, CDC13) delta 166.64, 154.05, 152.18, 127.10, 125.33, 1 14.73, 66.69, 48.33, 33.93, 27.94, 16.36. MS: 274 (M + 1). Anal. Calcd. for C15H19N3O2: C, 65.91; H, 7.01 ; N, 15.37; Found. 65.81, H, 6.66, N, 15.26.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Bromo-2-(2-bromoethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE BROAD INSTITUTE, INC.; DANA FARBER CANCER INSTITUTE, INC.; LEWIS A., Timothy; MUNOZ, Benito; DE WAAL, Lucian; GREULICH, Heidi; MEYERSON, Matthew; GECHIJIAN, Lara Nicole; WO2014/164704; (2014); A2;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 5414-19-7 as follows. Product Details of 5414-19-7

Part F:; To a DMF (9 mL) solution of Part E (1.08 g, 2.71 mmol) was added K2CO3 (1.12 g, 8.16 mmol), 18-crown-6 (0.21 g, 0.80 mmol), and bis (2-bromoethyl) ether (0.37 mL, 2.9 mmol). The slurry was stirred at 60C for 72 hr. Additional bis (2-bromoethyl) ether was added at 24 hr (0.4 mmol) and 48 hr (1.2 mmol). The solvent was stripped in vacuo, and the residue was partitioned between ethyl acetate (50 mL) and water (30 mL). The organic layer was separated, dried over MgS04, and evaporated to an oil. Recrystallization from diethyl ether produced 0. 88 g (69 %) of the desired compound in the form of a white solid. LCMS: itvz = 469.2 (M+H).

According to the analysis of related databases, 5414-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACIA CORPORATION; WO2005/42521; (2005); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 5414-19-7, These common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Under an argon atmosphere, NaH (4.11 g, 103 mmol, 60% purity) was added to a solution of ethyl 2-(4-bromophenyl)acetate (10 g, 41.1 mmol) in anhydrous DMF (200 mL) at 0C. The resulting mixture was stirred at 0C for 0.5 h. l-bromo-2-(2-bromoethoxy)ethane (9.5 g, 41.1 mmol) was added and then stirred at 0C for 1 h. NaH (4.11 g, 103 mmol, 60% purity) was added, and the reaction stirred at 0C for an additional 1 h. The resulting mixture was poured into saturated aqueous NH4Cl (200 mL) and extracted with ethyl acetate (3 x50 mL). The combined organic layers were washed with water (2 x50 mL), brine (50 mL), dried over Na2S04, filtered (1369) concentrated, and then purified by column chromatography (Si02, petroleum ether: ethyl (1370) acetate=5 : l) to give ethyl 4-(4-bromophenyl)tetrahydro-2//-pyran-4-carboxylate (5 2 g? 40%) as a yellow oil. 1H MR (400 MHz, CDCI3): d 7.43 (d, 2H), 7.22 (d, 2H), 4.17 (q, 2H), 3.95 (t, 2H), (1371) 3.58 (t, 2H), 2.52 (d, 2H), 1.96 (t, 2H), 1.21 (t, 3H); LCMS: 312.9 [M+H]+.

Statistics shows that 1-Bromo-2-(2-bromoethoxy)ethane is playing an increasingly important role. we look forward to future research findings about 5414-19-7.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; HUDSON, Andrew R.; CHEN, Mi; NAGASAWA, Johnny Y.; (265 pag.)WO2019/241751; (2019); A1;,
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Application of 5414-19-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 3-amino-1-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C. for 5 min before 2-bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. This mixture was stirred further at 25 C. for 5 h and at 75 C. for 72 h before it was cooled to 25 C., quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification of the residue on silica gel (gradient elution with 0% to 70% ethyl acetate in hexanes) afforded Cap-143, step a (180 mg, 31%) as a yellow solid. Rt=1.75 min (Cond.-MS-W1); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04.

The synthetic route of 1-Bromo-2-(2-bromoethoxy)ethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/249190; (2010); A1;,
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Ether | (C2H5)2O – PubChem

Synthetic Route of 5414-19-7,Some common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, molecular formula is C4H8Br2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of l-(4-bromo-phenyl)-cyclopropylamine (1 eq) in DMF in a 50 mL tube is added DIPEA (2 eq) and l-Bromo-2-(2-bromo-ethoxy)-ethane (1.1 eq). the reaction mixture is heated at 1000C for 16 hrs.. After cooling to room temperature, EtOAc and water are added. The combined organic layers are dried (MgSO4) and concentrated in vacuo to give the desired product.

The synthetic route of 5414-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS NV; MENET, Christel Jeanne Marie; BLANC, Javier; JOUANNIGOT, Nolwenn; HODGES, Alastair James; VAN ROMPAEY, Luc Juliaan Corina; FLETCHER, Stephen Robert; WO2010/10189; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Application In Synthesis of 1-Bromo-2-(2-bromoethoxy)ethane

A 500 mL round-bottom flask was charged with the product from Part E (29.1 g, 76 mmol), dimethylformamide (125 mL), 18-crown-6 (6 g, 22.8 mmol), potassium carbonate (31.5 g, 228 mmol), and 2-bromoethyl ether (11.7 mL, 83.5 mmol). The resulting mixture was heated to 60 C. with vigorous stirring for 44 hr. After cooling to room temperature, the reaction mixture was poured into 500 mL ice water. The mixture was then extracted with ethyl acetate (300 mL). Afterward, the organic layer was washed with brine (400 ml). The organic layer was then dried over magnesium sulfate, filtered, and concentrated in vacuo to form 40 g of a dark yellow oil. Purification via flash column chromatography on silica gel (3*6 inch column) afforded 30.2 g of a yellow oil product (88% yield). 1H NMR (CDCl3) delta 1.30 (m, 2H), 1.50 (s, 9H), 1.77 (m, 3H), 2.10 (dt, J=4.6, 12.6 Hz,2H), 2.31 (d, J=11.6 Hz, 2H), 2.94 (t, J=12.4 Hz, 2H), 3.25-3.33 (m, 4H), 3.77-3.84 (m, 2H), 3.95 (dd, J=4.2, 11.1, 2H), 4.48 (s, 2H), 7.25-7.35 (m, 5H); Electrospray mass spectrometry showed m/z=454 (M+H).

The synthetic route of 1-Bromo-2-(2-bromoethoxy)ethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 5414-19-7, These common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Intermediate 8 (1.70 g, 8.015 mmol) was dissolved in N, N-dimethylformamide (20 mL)Placed in a sealed tube,2,2′-dibromodiethyl ether (1.4 mL, 8.816 mmol) and N, N-diisopropylethylamine (2.7 mL, 16.03 mmol) were added.The reaction was heated to 100 C,Stir for 16 hours.Cooled to room temperature,Ethyl acetate was added,Washed,The organic phase is dried,Filtered and concentrated under reduced pressure,The crude product was purified by column chromatography,To give intermediate 9 (2.23 g) in 42% yield.

Statistics shows that 1-Bromo-2-(2-bromoethoxy)ethane is playing an increasingly important role. we look forward to future research findings about 5414-19-7.

Reference:
Patent; Shanghai Hansoh BioMedical Co., Ltd.; Jiangsu Hansoh Pharmaceutical Group Co., Ltd.; Zhao, Zhiming; Wu, Chenchen; Yu, Hongping; Xu, Yaochang; Pan, Zhongzong; Bao, Rudi; (26 pag.)CN106349180; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding some certain compound to certain chemical reactions, such as: 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 5414-19-7. 5414-19-7

To a room temperature mixture of the [T-BUTYL-2- ( {4- [4- (2-] ethoxyethoxy) phenyl] phenyl) sulfonyl) acetate product (4) from Part C (800 mg, 1.9 mmol) in 8 mL DMF was added 18-crown-6 (150 mg, 0.6 mmol), potassium carbonate (1.3 g, 9.5 mmol), and bis (2-bromoethyl) ether (480 mg, 2.1 mmol). The mixture was stirred at room temperature for 18 hr. Subsequently, no starting material (4) was detectable by HPLC. The resulting mixture was concentrated, diluted in cold ether, and filtered to produce 800 mg (86% yield) of the desired compound (5). LCMS: [[M+NA] =] 513.2.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1-Bromo-2-(2-bromoethoxy)ethane.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/811; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 5414-19-7 as follows. 5414-19-7

Under argon, 100 mg (0.30 mmol) of (4S)-1-(4-aminophenyl)-8-methoxy-N,4-dimethyl-4,5-dihydro-3H-2,3-benzodiazepine-3-carboxamide (Example 53.2A) were dissolved in 4 ml of N,N-dimethylacetamide, and 103 mg (0.44 mmol) of 1-bromo-2-(2-bromoethoxyl)ethane and 0.1 ml (0.59 mmol) of diisopropylethylamine were added. The mixture was stirred at 120 C. for three days. The reaction was added to water and extracted three times with ethyl acetate. The solvent was removed on a rotary evaporator and the residue was purified by flash chromatography. This gave 95 mg (79% of theory) of the desired product. [2019] UPLC/MS (Method 2): Rt=1.18 min; m/z=409 (M+H)+ [2020] 1H-NMR (300 MHz, CDCl3): delta=1.07 (d, 3H), 2.72 (dd, 1H), 2.86 (d, 3H), 2.95 (dd, 1H), 3.25 (m 4H), 3.71 (s, 3H), 3.89 (m, 4H), 5.19-5.30 (m, 1H), 6.12 (m, 1H), 6.67 (d, 1H), 6.89 (dd, 1H), 6.92 (d, 2H), 7.15 (d, 1H), 7.51 (d, 2H).

According to the analysis of related databases, 5414-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; Siegel, Stephan; Baeurle, Stefan; Cleve, Arwed; Haendler, Bernard; Fernandiez-Montalvan, Amaury Ernesto; Moenning, Ursula; Krause, Sabine; Lejeune, Pascale; Schmees, Norbert; Busemann, Matthias; Holton, Simon; Kuhnke, Joachim; US2015/203483; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 5414-19-7

[0971] To a DMF (9 mL) solution of Part E (1.08 g, 2.71 mmol) was added K2CO3 (1.12 g, 8.16 mmol), 18-crown-6 (0.21 g, 0.80 mmol), and bis(2-bromoethyl)ether (0.37 mL, 2.9 mmol). The slurry was stirred at 60C. for 72 hr. Additional bis(2-bromoethyl)ether was added at 24 hr (0.4 mmol) and 48 hr (1.2 mmol). The solvent was stripped in vacuo, and the residue was partitioned between ethyl acetate (50 mL) and water (30 mL). The organic layer was separated, dried over MgSO4, and evaporated to an oil. Recrystallization from diethyl ether produced 0.88 g (69%) of the desired compound in the form of a white solid. LCMS: m/z=469.2 (M+H).

The synthetic route of 5414-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem