Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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 36805-97-7, HPLC of Formula: C11H25NO2

To a hot (800C) solution of 4-bromo-3-methyl benzoic acid (3.00 g, 13.95 mmol) in toluene (250 ml_), N,N-dimethylformamide di-terf-butyl acetal (11.35 g, 50.2 mmol) was added. The mixture was stirred at 800C for 8 h and at rt for 16 h before another portion of lambda/,lambda/-dimethylformamide di-terf-butyl acetal (5.67 g, 25.1 mmol) was added. Stirring was continued at 80C for 16 h. The mixture was cooled to rt, diluted with EA and washed with sat. aq. NaHCO3-solution followed by water. The org. layer was separated, dried over Na2SO4, filtered, evaporated and dried under high vacuum at 400C to give terf-butyl 4-bromo-3-methyl benzoate as a pale yellow oil (2.31 g). LC-MS: tR = 1.10 min; [M+1]+ = not detectable; 1H NMR (CDCI3): £ 1.61 (s, 9H), 2.46 (s, 3H), 7.59 (d, J = 8.3 Hz, 1 H), 7.66 (d, J = 8.3 Hz, 1 H), 7.86 (s, 1 H).

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Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/109904; (2009); A1;,
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Reference of 1112210-82-8,Some common heterocyclic compound, 1112210-82-8, name is 1,3-Dibromo-5-isopropoxybenzene, molecular formula is C9H10Br2O, 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.

Synthesis of intermediate I-b: 3-bromo-5-isopropoxy-benzaldehydeTo a solution of I-a (4.630 g, 15.75 mmol) in dry Et20 (60 mL) under inert atmosphere was added dropwise at -78C a solution of n-butyl lithium in dry Et20 (6.3 mL, 15.75 mmol). The reaction mixture was stirred at -78C for 0.5 h. Then, dry DMF (1.35 mL) was added dropwise at -78C and the temperature was allowed to reach -40C over 1.5 h. A solution of HC1 (3N) was added and the crude product was extracted with Et20 (2 times), the organic layer was washed with water, then with a saturated solution of NaCl, dried over MgS04 and concentrated to give I-b as yellow oil in 82% yield. 1H RMN (300 MHz, CDC13) delta 9.89 (s, 1H), 7.54 (m, 1H), 7.29 (m, 2H), 4.60 (dt, J = 12.1, 6.0 Hz, 1H), 1.36 (t, J= 6.0 Hz, 6H).

The synthetic route of 1112210-82-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AB SCIENCE; BENJAHAD, Abdellah; MOUSSY, Alain; CHEVENIER, Emmanuel; PICOUL, Willy; LERMET, Anne; PEZ, Didier; MARTIN, Jason; SANDRINELLI, Franck; WO2013/14170; (2013); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., COA of Formula: C8H9BrO2

Example 26; Compound No.7; (S)-2-amino-N-(5-(3-methoxy-5-(piperidin-4-yloxy)phenyl)pent-4-ynyl)pent-4-ynamide; STEP A: 3-Bromo-5-methoxyphenol; 1-Bromo-3,5-dimethoxy-benzene (0.217 g, 0.001 mol) and KCN (0.20 g, 0.003 mol) were taken up into DMSO (10 mL) and the resulting mixture stirred at 120 C. for six hours, then at 150 C. overnight. The mixture was maintained at this temperature, with stirring for another day. The reaction was then quenched with water and the resulting mixture extracted with EtOAc. The organic layer was washed with saturated NaHCO3, brine, then dried over sodium sulfate and the solvent removed in vacuo. The resulting residue was purified on normal phase chromatography (Heptane/EtOAc) to yield 3-bromo-5-methoxyphenol. MH+ 203, 205

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Parker, Michael H.; Hlasta, Dennis J.; Huang, Yifang; Reitz, Allen B.; Lawson, Edward C.; Schubert, Carsten; Strobel, Eric; Tounge, Brett A.; White, Kimberly; Winters, Michael P.; Ghosh, Shyamali; US2011/105562; (2011); A1;,
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Related Products of 36942-56-0,Some common heterocyclic compound, 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene, molecular formula is C8H9BrO, 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.

Step 2: (4-Bromo-2-methoxy-5-methylphenyl)(4-fluorophenyl)methanone4-Fluorobenzoyl chlo?de (1.40 mL, 11.9 mmol) was added dropwise to a suspension ofAlCl3 (1.73 g, 13.0 mmol) in 1 ,2-dichloroethane (30 mL) at room temperature. After 15 mm a solution of 3-bromo-4-methylanisole (2.17 g, 10.8 mmol) in 1 ,2-dichloroethane (3 mL) was added dropwise. The resulting mixture was stirred for 2 h, poured into 200 mL of ice-water, stirred for 20 min and extracted with CHCl3 (3x). The combined organics were washed with 5% aq. NaHCO3, brme, d?ed (Na2SO4) and concentrated. The residue was subjected to chromatography on silica gel (EtOAc-hexane, 5:95) affording the title compound. 1H NMR (500 MHz, acetone-^): delta 7.86 (m, 2H), 7.38 (s, IH), 7.31-7.26 (m, 3H), 3.76 (s, 3H), 2.39 (s, 3H).

The synthetic route of 36942-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2006/99735; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1462-37-9, name is ((2-Bromoethoxy)methyl)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 1462-37-9, COA of Formula: C9H11BrO

To a solution of methyl 4-hydroxyphenylacetate (500 mg, 3.01 mmol) in N,N-dimethylformamide (2.0 ml), cesium carbonate (1.00 g, 3.07 mmol) and benzyl 2-bromoethyl ether (0.5 ml, 3.2 mmol) were added, and the mixture was stirred at 50°C for 2 hours and then cooled to room temperature. Distilled water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water, dried, and then concentrated under a reduced pressure. The residue was purified via flash chromatography (silica gel, n-hexane/ethyl acetate) to give a title compound (679 mg, 2.26 mmol, 75 percent) as a colorless liquid. 1H-NMR (400 MHz, CDCl3) delta: 3.56 (2H, s), 3.68 (3H, s), 3.82 (2H, t, J = 4.88 Hz), 4.14 (2H, t, J = 4.88 Hz), 4.63 (2H, s), 6.88 (2H, d, J = 8.5 Hz), 7.18 (2H, d, J = 8.5 Hz), 7.27-7.39 (5H, m).

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Reference:
Patent; TORAY INDUSTRIES, INC.; EP2009006; (2008); A1;,
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Electric Literature of 20469-65-2, 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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A. To a solution of 1-bromo-3,5-dimethoxybenzene (3.01 g, 13.9 mmol) in dry THF (25 mL) at -78C under argon was added a solution of n-BuLi (2.2 M in hexanes, 7.00 mL, 15.4 mmol) dropwise and the mixture stirred for 40 mm. A solution of iodine in dry THF (20 mL) was then added dropwise and the reaction allowed to stir for an additional 45 mm at -78C before quenching with 20% aqueous Na25203 (45 mL) and warming to room temperature. The mixture was diluted with EtOAc (50 mL), the layers separated and the organic layer washed with brine (50 mL), dried (Mg504) and concentrated to a yellow solid (3.12 g). Purification of the crude product by chromatography on silica gel (20% EtOAc/hexanes) gave 1-iodo-3,5- dimethoxybenzene (Compound No. 31, 2.01 g, 55%) as a white solid.

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-3,5-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AQUINOX PHARMACEUTICALS INC.; MACKENZIE, Lyoyd, F.; MACRURY, Thomas, B.; HARWIG, Curtis; BOGUCKI, David; RAYMOND, Jeffery, R.; PETTIGREW, Jeremy, D.; KHLEBNIKOV, Vladimir; SHAN, Rudong; WO2014/110036; (2014); A1;,
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Synthetic Route of 175278-09-8, 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. 175278-09-8, name is 4-Bromo-2-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 58 5-[4-amino-3-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile 4-Bromo-2-(trifluoromethoxy)aniline (1.3 g, 5.0 mmol), 5-cyano-1-methyl -1H-pyrrol-2-ylboronic acid (0.9 g, 6.0 mmol), potassium fluoride (0.96 g, 16.5 mmol), and tris(dibenzylideneacetone)dipalladium (0.12 g, 0.12 mmol) were placed in an oven dried flask under nitrogen and THF (12.5 mL) was added. Tri-t-butylphosphine (10 wt % in hexane) (0.356 mL, 0.24 mol) was added and the reaction was stirred for 16 hours. The reaction mixture was filtered through silica, rinsed with ethyl acetate, and concentrated. The crude product was pre-adsorbed onto the Celite reagent and purified via Isco chromatography (the Redisep column, silica, gradient 5-30% ethyl acetate in hexane) to afford 1.0 g (71%) of 5-[4-amino-3-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile. HPLC purity 98.2% at 210-370 nm, 9.6 min.; the Xterra RP18 instrument, 3.5mu, 150*4.6 mm column, 1.2 mL/min., 85/15-5/95 (Ammon. Form. Buff. PH=3.5/ACN+MeOH) for 10 min., hold 4 min. MS (ES) m/z 281.

The synthetic route of 4-Bromo-2-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2007/27201; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2674-34-2, name is 1,4-Dibromo-2,5-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 2674-34-2, Product Details of 2674-34-2

Reacting a compound of formula 4 with sodium hydride in tetrahydrofuran as a solvent at -78 C for two hours,At the same time, the compound of formula 5 was reacted with n-butyllithium using tetrahydrofuran as a solvent at -78 C for one hour, and then mixed at -78 C for two hours.Add N, N-dimethylformamide and stir for five minutes, add methyl iodide to react at room temperature for twelve hours, add water to quench the reaction,The crude product was subjected to column chromatography with ethyl acetate and petroleum ether system to obtain intermediate formula 6 required for Suzuki Coupling Reaction, with a reaction yield of 52%.

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, 1,4-Dibromo-2,5-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chinese Academy Of Sciences Physics And Chemistry Technology Institute; University of the Chinese Academy of Sciences; Cong Huan; Fan Yangyang; (9 pag.)CN110272332; (2019); A;,
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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. COA of Formula: C4H8Br2O

Step a Intermediate 207 -Bromophenyl 2-ethyltetrahydro-2H-pyran-4-carboxylate A mixture of NaH (60% in mineral oil) (2.057 g, 51.4 mmol) in DMF (67 ml) stirred at 0 C was treated dropwise with a mixture of ethyl 2-(4-bromophenyl)acetate (5 g, 20.57 mmol) and 1 -bromo-2-(2-bromoethoxy)ethane (2.59 ml, 20.57 mmol) in 3 ml of diethyl ether. The mixture was allowed to warm to r.t. and stirred for 17 h. Mixture was quenched with water and sat. NH4CI. The mixture was extracted with EtOAc (x 3) and then organics washed with brine (x 3) and dried (MgS04), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Si02; 0 – 100 % EtOAc in petrol) to yield 4-bromophenyl 2-ethyltetrahydro-2H-pyran-4- carboxylate as a pale yellow oil (2.88 g, 45 %). ? NMR (400 MHz, CD2C12) 57.46 – 7.56 (m, 2H), 7.32 (m, 2H), 4.15 (m, 2H), 3.84 – 3.98 (m, 2H), 3.50 – 3.63 (m, 2H), 2.38 – 2.56 (m, 2H), 1.95 (m, 2H), 1.21 (m, 3H)

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; RUPRAH, Parminder, Kaur; MERCHANT, Kevin, John; WALSH, Louise, Marie; KERR, Catrina, Morven; FIELDHOUSE, Charlotte; HARRISSON, David; MAINE, Stephanie; HAZEL, Katherine; WO2013/27001; (2013); A1;,
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Application of 13321-74-9, These common heterocyclic compound, 13321-74-9, name is 4-Bromo-2,5-dimethoxytoluene, 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.

General procedure: A flask containing LiCl (980 mg,23.1 mmol), 2-bromo-4-fluoroanisole (1.0 mL, 7.7 mmol), DCMA (1.8 mL,8.4 mmol) and ethyl 3-ethoxyacrylate (3.3 mL, 23 mmol) in 1,4-dioxane(20 mL) was degassed by passing a stream of nitrogen through the mixturefor 10 min. Bis(tri-t-butylphosphine) palladium(0) (166 mg, 0.32 mmol) wasadded, and reaction mixture was heated at reflux under nitrogen for 16 h. Thebrown mixture was then cooled and partitioned between ethyl acetate andwater. The layers were separated, and the organic layer was washedsequentially with aqueous NH4Cl and brine, followed by drying over Na2SO4.The mixture was filtered, and the filtrate was concentrated under reducedpressure to give an oil which was purified by flash chromatography on silica(40 g, 10-50% ethyl acetate in heptane) to afford 22c as an orange oil (1.93 g,92%) as an inseparable mixture of E- and Z-isomers: 1H NMR (CDCl3, 500 MHz)alkene protons d: 5.21, 5.33 ppm (1:1 ratio); LCMS (ES): 269.2 (MH). HRMSCalcd for C14H17FO: 269.1184. Found: 269.1196.

The synthetic route of 13321-74-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kohrt, Jeffrey T.; Conn, Ed; Maguire, Robert; Wright, Stephen W.; Singer, Robert; Tetrahedron Letters; vol. 54; 51; (2013); p. 7065 – 7068;,
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