Category: ethers-buliding-blocks

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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Reference of 150-78-7,Some common heterocyclic compound, 150-78-7, name is 1,4-Dimethoxybenzene, molecular formula is C8H10O2, 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.

Example 2: Preparation of 2,5-dibromo-1 ,4-dimethoxybenzene (2); [00103] In a one liter round-bottom flask, a solution of bromine (35.2 g, 220 mmol) in chloroform (50 ml) was added dropwise to a solution of 1 ,4- dimethoxybenzene (13.8 g, 100 mmol) in chloroform (400 ml) under 00C. After stirring for 3 hours, 100 ml of saturated Na2CO3 solution was added. The organic layer was washed with water, brine, and dried over sodium sulfate. The solvent was removed on a rotary evaporator and the residue was performed recrystallization from ethanol to afford pure 2,5-dibromo-1 ,4- dimethoxybenzene (25.8 g, 85%). 1HNMR (CDCI3) 57.128 (s, 2 H), 3.873 (s, 6 H).

The synthetic route of 150-78-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NATIONAL UNIVERSITY OF SINGAPORE; WO2006/93467; (2006); A1;,
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Electric Literature of 6851-80-5, The chemical industry reduces the impact on the environment during synthesis 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, I believe this compound will play a more active role in future production and life.

a N-(2-Methoxybenzyl)–N-(methyl)aminoacetonitrile A mixture of 2.0 g (13.2 mmole) of N-methyl-2methoxybenzylamine, 0.99 g (13.2 mmole) of chloroacetonitrile, and 2.80 g (26.5 mmole) of powdered sodium carbonate was stirred in 30 mL of acetone at room temperature for 4 days. The mixture was concentrated in vacuo and the residue purified by flash chromatography on 130 g of silica gel eluding with 83:17 hexanes: ethyl acetate to give 2.2g (87%) of an oil. 1 H NMR (CDCl3, 400 MHz, ppm): delta 2.43 (s, 3H), 3.48 (s, 2H), 3.62 (s, 2H), 3.83 (s, 3H), 6.88 (d, 1H), 6.93 (t, 1H), 7.2-7.3 (m, 2H).

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-(2-Methoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US5610165; (1997); A;,
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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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Application of 1484-26-0, These common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, 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.

To a stirred solutionof 3-(benzyloxy)aniline 10b (1.0 equiv.) in ethylformate (3 mL),catalytic amount of pTsOH monohydrate was added. The reactionmixture was stirred at rt for 3 days and the resulting mixture wasextracted with ethyl acetate. Organic layers were collected, washedwith water and brine, dried over anhydrous MgSO4 and evaporatedgiving the product 11b as white solid in 80percent yield.xNMR: mixture of two rotamers (approx. 1:1) 1H (600 MHz,CDCl3): d 8.67 (d, J 10.0 Hz, 1H), 8.32 (s, 1H), 7.97e7.67 (m, 22H),5.05 (s, 2H), 5.03 (s, 2H).

Statistics shows that 3-Benzyloxyaniline is playing an increasingly important role. we look forward to future research findings about 1484-26-0.

Reference:
Article; Surmiak, Ewa; Neochoritis, Constantinos G.; Musielak, Bogdan; Twarda-Clapa, Aleksandra; Kurpiewska, Katarzyna; Dubin, Grzegorz; Camacho, Carlos; Holak, Tad A.; Doemling, Alexander; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 384 – 407;,
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Adding a certain compound to certain chemical reactions, such as: 2734-70-5, name is 2,6-Dimethoxyaniline, 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 2734-70-5, Safety of 2,6-Dimethoxyaniline

To a solution of pentanenitrile (310 mg, 3.7 mmol) and 2-methoxy-6-methylaniline (518 mg, 3.40 mmol) in toluene (13 mL) at RT was added a solution of trimethylaluminum in toluene (1.7 mL, 3.4 mmol) at 0 °C. The reaction mixture was heated at 110 °C for 1 h. The cooled reaction mixture was quenched by the addition of a saturated solution of Rochelle’s salt (5 mL) and stirred at RT for 30 min. The reaction mixture was extracted with EtOAc (3×20 mL). The combined organic portion was washed with brine, dried over MgS04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography elution with 20-100percent EtOAc hexanes to give Compound la (450 mg, 56percent) as a brown oil. LCMS (Method D) retention time = 0.65 min, m/z = 237.1 (M+H)+. NMR (500MHz, chloroFORM-d)? 6.88 (t, J=8.4 Hz, 1H), 6.51 (d, J=8.3 Hz, 2H), 4.68 – 3.89 (m, 2H), 3.71 (s, 6H), 2.33 (br. s., 2H), 1.84 -1.52 (m, 2H), 1.49 -1.24 (m, 2H), 0.89 (br. s., 3H).

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Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; TORA, George, O.; FINLAY, Heather; JIANG, Wen; MENG, Wei; ZHANG, Xiaojun; (303 pag.)WO2017/218633; (2017); A1;,
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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. 109-85-3, name is 2-Methoxyethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: ethers-buliding-blocks

A solution of 6-amino-4-fluoronicotinonitrile (intermediate 21, 1.10 g, 8.02 mmol) in DMA (20 ml)was treated with 2-methoxyethylamine (2.07 ml, 24.1 mmol) and DIPEA (4.20 mL, 24.1 mmol),heated to 50 C and stirred for 15 h. The reaction mixture was cooled to room temperature and concentrated. The crude material was purified by normal phase chromatography (24 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100). The product containing fractions were concentrated and dried under vacuum to give the title compound as an off-white solid.

The synthetic route of 109-85-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BUSCHMANN, Nicole; FAIRHURST, Robin Alec; FURET, Pascal; KNOePFEL, Thomas; LEBLANC, Catherine; MAH, Robert; NIMSGERN, Pierre; RIPOCHE, Sebastien; LIAO, Lv; XIONG, Jing; ZHAO, Xianglin; HAN, Bo; WANG, Can; WO2015/59668; (2015); 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).

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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.

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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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