Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, belongs to ethers-buliding-blocks compound, 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, Recommanded Product: 5414-19-7

A solution of ethyl 3-aminothieno[2,3-bjpyridine-2-carboxylate (500 mg, 2.25 mmol), 1-bromo-2-(2-bromoethoxy)ethane (1.38 g, 6 mmol) and Cs2CO3 (1.63 g, 5 mmol) in DMA (30mL) was stirred for 3 hours at 80C. H20 (50 mL) was added and it was extracted withEA(3x). The organic layer was concentrated and purified by reverse phase C18 columnchromatography (MeCN/H20) to give desired compound as light brown oil. (500 mg, 76 %). ESI-MS m/z: 293.2 [M+Hf

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; ENANTA PHARMACEUTICALS, INC.; SHOOK, Brian, C.; KIM, In, Jong; BLAISDELL, Thomas, P.; YU, Jianming; PANARESE, Joseph; OR, Yat, Sun; (434 pag.)WO2017/15449; (2017); A1;,
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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.

A solution of 2-(4-phenylthiazol-2-yl)acetonitrile (0.84 g, 4.19 mmol) in THF (25 mL) was cooled to 0 C. NaH was added (0.5 g, 60% dispersion in oil) portionwise over 10 min. The resulting mixture was allowed to warm up to room temperature and stirred for 20 min. 2-Bromoethyl ether (1.58 mL, 12.5 mmol) was added dropwise. The reaction mixture was further stirred at room temperature for 1 h and then quenched with saturated NH4Cl solution. The reaction mixture was diluted with EtOAc and the organic layer was washed with H2O and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 60-120 mesh, eluent 4-8% EtOAc in petroleum ether) to afford 4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-carbonitrile (0.97 g, yield 85%) as a yellow solid: 1H NMR (300 MHz, CDCl3) delta 7.91-7.94 (m, 2H), 7.51 (s, 1 H), 7.37-7.48 (m, 3H), 4.07-4.14 (m, 2H), 3.87-3.96 (m, 2H), 2.32-2.43 (m, 4H). MS (ESI) m/z: Calculated for C15H14N2OS: 270.08; found: 271.2 (M+H)+.

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

Reference:
Patent; Tempero Pharmaceuticals, Inc.; BALOGLU, Erkan; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby; EP2533783; (2015); B1;,
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74137-36-3, The chemical industry reduces the impact on the environment during synthesis 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, I believe this compound will play a more active role in future production and life.

Tris(dibenzylideneacetone)dipalladium(0) (6.53 g, 7.15 mmol) was added in one portion to a stirred solution of the bromide of Preparation 1 (38.0 g, 143 mmol), 1,1′-bis(diphenylphosphino)ferrocene (9.3 g, 16.8 mmol) and zinc cyanide (20.0 g, 172 mmol) in N,N-dimethylformamide (300 ml) at room temperature under nitrogen. The reaction was heated at 100° C. for 14 hours and cooled to room temperature. Water (1500 ml) was added and the mixture was extracted with ethyl acetate (3.x.500 ml). The combined organics were filtered and the filtrate was washed with water (500 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The resulting solid was triturated with toluene (1000 ml) to provide the title compound (18.0 g) as a tan solid. 1H-NMR (300 MHz, CDCl3): delta=3.83 (3H, s), 7.31 (2H, s), 7.48 (1H, s).

The chemical industry reduces the impact on the environment during synthesis 1,3-Dibromo-5-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pfizer Inc.; US2005/54707; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1663-61-2, name is (Triethoxymethyl)benzene, belongs to ethers-buliding-blocks compound, 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 1663-61-2, Safety of (Triethoxymethyl)benzene

b. 1-Azidoethyl-2,4-dibenzoylmannose To a 1.0 L, 3-neck flask containing a stir bar, nitrogen inlet and 300 mL of anhydrous acetonitrile was added 25 gm 1-azidoethylmannose (100.4 mmole), and 50 mL triethyl orthobenzoate (220 mmole, 2.2 equiv.). The resulting slurry was stirred at room temperature and 0.8 mL (10 mmole) trifluoroacetic acid (TFA) was added neat. The solution cleared within 10 minutes and stirring was continued for an additional two hours, then 25 mL of 10percent aqueous TFA was added and stirring was continued for an additional 2 hours to hydrolyze the intermediate to the ester isomers. The solvent was evaporated under vacuum to a viscous oil, which was triturated with 50 mL DCM and again evaporated to a viscous oil. Toluene (70 mL) was added to the residue and the viscous solution was seeded with 2,4-dibenzoylazidoethylmannose. A fine precipitate formed within 15 minutes and stirring was continued overnight at room temperature. The resulting heavy suspension was set in the freezer for 2-4 hours, then filtered and the solid washed with ice cold toluene (2*10 mL). The solid was air dried to a constant weight to give 21 gm (TY 22.85 gm 50percent isomeric purity) of ?95percent isomeric purity. The product was taken into 40 mL toluene, stirred for 1 hour and then set in the freezer for an additional 2 hours. The solid was filtered and washed (2*10 mL) with ice cold toluene and air dried to a constant weight to give 18.5 gm of the single isomer product 2,4-dibenzoylazidoethylmannose in 83percent yield. The mother liquors contained the undesired isomer and a small amount of the desired isomer. The reaction was monitored by TLC: SG (Hexane/Ethyl Acetate 7/3) Starting Material Rf 0.0, orthoester intermediate Rf 0.9. (Hexane/Ethyl Acetate: 8/2) SM Rf 0.8, desired isomer Rf 0.4, un-desired isomer Rf 0.2 1H NMR 300 MHz (CDCl3) delta 8.12 (t, 4H), 7.66 (t, 2H), 7.5 (m, 4H), 5.56 (t, 1H), 5.48 (m, 1H), 5.14 (m 1H), 4.5 (dd, 1H), 4.0 (m, 2H), 3.8 (m, 3H), 3.56 (m, 1H), 3.44 (m, 1H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SMARTCELLS, INC.; Chen, Zhiyu; Lancaster, Thomas M.; Zion, Todd C.; US2013/190475; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, belongs to ethers-buliding-blocks compound, 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 17715-69-4, Safety of 1-Bromo-2,4-dimethoxybenzene

General procedure: Synthesis of 4′-methoxybiphenyl-4-carbonitrile. A reaction vessel equipped with filtration frit was charged with polystyrene resin-bound benzyl(di-tert-butyl)phosphonium chloride (6.20 mg, 4% mol, 100-200 mesh resin containing 1.60 mmol/g phosphonium hydrochloride) and flushed with argon. Next, 5mL of degassed dioxane was added followed by 20 mL of diisopropylamine and reaction mixture was agitated for 1 h at room temperature. Subsequently, the solvent was removed and the resin washed with degassed dioxane (3×5 mL). The resin was resupended in dioxane (5.0 mL) and Pd2(dba)3·CHCl3 (5.20 mg, 2% mol) added and the reaction mixture was agitated for 12 h at room temperature. The Pd-doped resin becomes black in colour. The solvent was removed and catalyst washed with degassed dioxane (3×5 mL). 4-Bromobenzonitrile (45.5 mg, 0.25 mmol), 4-methoxyphenylboronic acid (42.0 mg, 0.28 mmol), Cs2CO3 (179.2 mg, 0.55 mmol), 5 mL of degassed dioxane were added and the suspension agitated for 72h at room temperature. The solution was filtered and the Pd-doped catalyst re-suspended and washed with degassed dioxane (3 x 5 mL). Evaporation of the combined dioxane extracts under vacuum and purification by chromatography on silica gel (ethyl acetate/hexane 1:9) afforded the title compound (41 mg, 80%). All entries reported in table 2 were conducted under the above conditions.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Ullah, Ehsan; McNulty, James; Sliwinski, Marcin; Robertson, Al; Tetrahedron Letters; vol. 53; 31; (2012); p. 3990 – 3993;,
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Adding a certain compound to certain chemical reactions, such as: 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, belongs to ethers-buliding-blocks compound, 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 175278-17-8, Recommanded Product: 2-Bromo-4-(trifluoromethoxy)aniline

To a mixture of 2-bromo-4-(trifluoromethoxy)aniline (1.00 mmol), triethylamine (1.5 mmol) and P(o-tol)3 (0.40 mmol) in DMF (0.5 M) in a glass pressure tube under nitrogen gas were added ethyl acrylate (1.0 mmol) and palladium acetate (0.20 mmol). The tube was sealed and heated to 120 0C for 18 h. The resulting solution was concentrated under vacuum and purified by column chromatography. Retention time (min) = 2.467, method [1], MS(ESI) 276.1 (M+H).

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, 2-Bromo-4-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; SHAM, Hing, L.; KONRADI, Andrei, W.; HOM, Roy, K.; PROBST, Gary, D.; BOWERS, Simeon; TRUONG, Anh; NEITZ, R., Jeffrey; SEALY, Jennifer; TOTH, Gergely; WO2010/91310; (2010); A1;,
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17061-62-0, name is Bis(4-methoxybenzyl)amine, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 17061-62-0

To a stirred solution of 100.1 (100 g, 0.39 mol) in DCM (1 L) was added TEA (71 mL, 0.51 mol), followed by dropwise addition of methanesulfonyl chloride (36 mL, 0.47 mol). The internal temperature was kept between 5-10 C during the addition of methane sulfonyl chloride. Once the addition was complete, the cooling bath was removed and the mixture was stirred at RT until TLC analysis indicated that the reaction was complete. Thereafter, water (1 L) was added, the layers were separated and the aqueous layer was extracted with DCM (2 x 500 mL). The combined organic layers were washed with brine (2 x 1 L), dried over Na2SO4, and concentrated in vacuo. The residue was purified on a silica gel column, employing a gradient of 10-80% EtOAc in hexanes, to afford 120 g (0.36 mol, 92%) of 101.0 as white solid.1H-NMR (400 MHz, CDCl3) delta 7.26 (dd, J=2.12, 6.60 Hz, 4H) 6.91 (dd, J=2.12, 6.62 Hz, 4H) 4.28 (s, 4H) 3.83 (s, 6H) 2.75 (s, 3H).

The synthetic route of 17061-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; KREIMAN, Charles; (308 pag.)WO2018/93579; (2018); A1;,
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Related Products of 60789-54-0, These common heterocyclic compound, 60789-54-0, name is ((4-Bromobutoxy)methyl)benzene, 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.

Reference Example 18 4-Benzyloxy-3-(4-benzyloxybutoxy)benzonitrile 4-Benzyloxy-3-hydroxybenzonitrile (3.4g) and potassium carbonate (6.3g) were dissolved in N,N-dimethylformamide (20mL). To the mixture was added benzyl 4-bromobutylether (3mL), and the mixture was stirred at 50C for 16 hours. To the reaction mixture was added dropwise 2mol/L hydrochloric acid (4mL), and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent:ethyl acetate/hexane=1/5) to give the title compound (5.9g). 1H-NMR (CDCl3) delta ppm: 1.70-2.10 (4H, m), 3.55 (2H, t, J=6.1Hz), 4.04 (2H, t, J=6.5Hz), 4.49 (2H, s), 5.17 (2H, s), 6.90 (1H, d, J=8,2Hz), 7.08 (1H, d, J=1.9Hz), 7.19 (1H, dd, J=1.9Hz, 8.2Hz), 7.24-7.45 (10H, m)

Statistics shows that ((4-Bromobutoxy)methyl)benzene is playing an increasingly important role. we look forward to future research findings about 60789-54-0.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP1698635; (2006); A1;,
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Synthetic Route of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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 14: step a 4-Bromo-2-isothiocyanato-1-methoxy-benzene A solution of sodium bicarbonate (3.74 g, 44.5 mmol) in water (75 mL) was added to commercially available 5-bromo-2-methoxy-phenylamine (3 g, 14.8 mmol) in chloroform (75 mL). Thiophosgene (1.42 mL, 18.6 mmol) was then added. The biphasic solution was stirred at room temperature for 1 h. The phases were separated and the aqueous phase was extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and concentrated, yielding the crude title compound as an off-white solid.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; JACKSON, Paul Francis; Manthey, Carl; Rhodes, Kenneth; Scannevin, Robert; Leonard, Kristi Anne; Barbay, Joseph Kent; Todd, Matthew; Springer, Barry A.; US2012/302573; (2012); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 589-10-6, name is (2-Bromoethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of (2-Bromoethoxy)benzene

General procedure: Anhydrous K2CO3 (1.2 M equiv) was added to the solution of GA or compound 42 (0.2 mmol) and halogenating agents (1.2 M equiv) in dry DMF (5 mL). The reaction mixture was stirred at room temperature until the starting material was not observed by TLC. The mixture was treated with H2O (20 mL), the aqueous layer was extracted with EtOAc (2×20mL). The joined organic extracts were washed three times with H2O (60 mL) and saturated NaCl (60 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to dryness under reduced pressure. The residue was chromatographed using a silica gel column to afford the pure target products.

According to the analysis of related databases, 589-10-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Li-Jun; Geng, Chang-An; Ma, Yun-Bao; Huang, Xiao-Yan; Luo, Jie; Chen, Hao; Zhang, Xue-Mei; Chen, Ji-Jun; Bioorganic and Medicinal Chemistry Letters; vol. 22; 10; (2012); p. 3473 – 3479;,
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