Author: Jessica.F

These common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, 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. category: ethers-buliding-blocks

Preparation of A/-(3-(5-(3-(trifluoromethoxy)phenylamino)pyridin-3- vDphenvDacetamide (Compound 152) [00296] A mixture of 3,5 -dibromopyridine (2.0Og, 8.44mmol), 3-acetamidophenylboronic acid (1.5 Ig, 8.44mmol), potassium carbonate (1.17g, 8.44mmol) and palladium (tetrakis)triphenylphosphine (294mg, 0.025mmol) in DME/H20 (4OmL, 3:1) was refluxed for 16h. The solvent was removed in vacuo, the resulting yellow solid was partitioned between DCM (30OmL) and brine (15OmL) and the two layers were separated. The aqueous layer was extracted further with DCM (2x10OmL) and the combined extracts were dried over anhydrous MgSO4. Evaporation of the solvent afforded crude iV-(3-(5-bromopyridin-3- yl)phenyl)acetamide in 74percent purity (LC). This material (1.2Og, 4.12mmol), 3- (trifluoromethoxy)aniline (66IuL, 4.95mmol), cesium carbonate (3.36g, 10.3mmol), palladium bis-acetate (47mg, 0.21mmol) and Xantphos (238mg, 0.41mmol) were dissolved in dioxane (7.5mL) and the resulting mixture was heated, under microwave activation, at 15O0C for 20mins. The crude mixture was partitioned between EtOAc (10OmL) and brine (10OmL) and the two layers were separated. The aqueous layer was extracted further with EtOAc (10OmL), the combined layers were dried over anhydrous MgSO4 and evaporated to dryness. The resulting solid was purified by column chromatography eluting using a gradient (EtOAc/hexanes 0:1 v/v to EtOAc/hexanes 1 :0 v/v) to afford 590mg (37percent) of the title compound. LCMS RT= 1.59min, MH+ 388.2. 1U NMR (d6-DMSO): 10.07 (IH, s), 8.83 (IH, s), 8.39 (IH, d, J2.5), 8.36 (IH, d, J 1.9), 7.91 (IH, s), 7.65 (IH, t, J2.2), 7.60 (IH, d, J 8.0), 7.45-7.33 (3H, m), 7.17 (IH, dd, J 8.2 1.8), 7.02 (IH, s), 6.84 (IH, d, J 8.2), 2.07 (3H, s).

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

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; DAVIS, Paul James; WO2010/57833; (2010); A1;,
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These common heterocyclic compound, 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, 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 2-Fluoro-1,4-dimethoxybenzene

To a solution of 2-fluoro-l,4-dimethoxybenzene (8.1 g, 52.0 mmol) in anhydrous THF at -78 C, n-BuLi (2.5 M in hexane, 22 mL, 55 mmol) was added dropwise. The resulting mixture was stirred at -78 C for 1 h, and then ethyl chloroformate (5 mL, 52.1 mmol) was added dropwise. The reaction mixture was stirred at -78 C for additional 2 h and quenched with water (200 mL). The mixture was extracted with ethyl acetate (2×180 mL). The combined organic layers were washed with brine (200 mL), dried (Na2S04), and concentrated in vacuo. The residue was purified by silica gel column chromatography (1 :5 EtOAc/petroleum ether) to give ethyl 2-fluoro-3,6-dimethoxybenzoate (8.1 g).

The synthetic route of 2-Fluoro-1,4-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; KAHRAMAN, Mehmet; GOVEK, Steven, P.; NAGASAWA, Johnny, Y.; SMITH, Nicholas, D.; WO2011/156518; (2011); A2;,
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Adding a certain compound to certain chemical reactions, such as: 60876-70-2, name is 1-Bromo-4-(tert-butoxy)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 60876-70-2, Safety of 1-Bromo-4-(tert-butoxy)benzene

Compound (T-22) (179.7 g, 784.5 mmol), bispinacolato diborane (239.0 g, 941.4 mmol), potassium acetate (92.4 g, 941.4 mmol), bis(diphenylphosphino ferrocene dichloropalladium(II) (10.0 g, 13.7 mmol) and 1,3-dioxane (1,000 mL) were mixed, and the resulting mixture was stirred at 90 C. for 4 hours. The reaction mixture was allowed to cool to room temperature, and then poured into water, and subjected to extraction with heptane (800 mL). The extracted layer was washed with water (1,000 mL) and saturated brine (500 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (eluent:heptane) to obtain compound (T-23) (182 g, 659 mmol, 84.10).

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; JNC Co., Ltd.; JNC Petrochemical Co., Ltd.; Kobayashi, Masahide; Goto, Yasuyuki; Goto, Mayumi; (103 pag.)KR2016/2826; (2016); A;,
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588-96-5, name is p-Bromophenetole, 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. Product Details of 588-96-5

Example XIV.1 2-{4-[1-(4-Ethoxy-phenyl)-piperidin-4-yl]-phenyl}-propionic acid 1.00 g (4.04 mmol) 2-(4-Piperidin-4-yl-phenyl)-propionic acid methyl ester (XI.3) are added to a mixture of 813 mg (4.04 mmol) 1-bromo-4-ethoxy-benzene, 1.60 g (97%, 16.2 mmol) sodium tert-butyrat, 483 mg (1.62 mmol) 2-(di-tert-butylphosphino)biphenyl and 370 mg (0.40 mmol) tris-(dibenzylidenaceton)-dipalladium(0) in 10 mL 1,4-dioxane. The mixture is stirred for 12 h at 70 C. After that time, the precipitate is filtered off and washed with ACN and diethyl ether. The residue is purified by HPLC (column: Waters XBridge 50; eluent A: water+0.3% NH4OH, eluent B: MeOH) to yield the desired product. C22H27NO3 (M=353.5 g/mol) ESI-MS: 354 [M+H]+Rt (HPLC): 1.69 min (method C)

The synthetic route of 588-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROTH, Gerald Juergen; FLECK, Martin; LEHMANN-LINTZ, Thorsten; NOSSE, Bernd; US2013/143876; (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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

B) (4S)-Lambda/-((1 S)-1-r4-(methyloxy)phenyllethyll-3.4-dihvdro-2H-pyranor3.2-lpyridin-4- amine: To a solution of crude 2,3-dihydro-4/-/-pyrano[3,2-]pyridin-4-one (2.43 g) in 1 ,2- dichloroethane was added {(1S)-1-[4-(methyloxy)phenyl]ethyl}amine EPO (2.49 g, 16.5 mmol) and acetic acid (1.4 ml_, 24.5 mmol). The reaction mixture was stirred for 1 hour, then sodium triacetoxyborohydride (5.18 g, 24.4 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours, then diluted with dichloromethane and quenched with saturated aqueous sodium bicarbonate solution. The organic layer was separated and dried over sodium sulfate. Filtration and concentration, followed by flash chromatography (0 to 10% aqueous NH4OH in acetonitrile) provided (4S)- Lambda/-{(1S)-1-[4-(methyloxy)phenyl]ethyl}-3,4-dihydro-2/-/-pyrano[3,2-/j]pyridin-4-amine (1.90 g, 38% two step yield) as a brown oil. 1H NMR (400 MHz, CDCI3) delta 8.15 (dd, J = 3.0, 3.0 Hz, 1 H), 7.35 (d, J = 8.6 Hz, 2 H), 7.07 (d, J = 2.8 Hz, 2 H), 6.86 (d, J = 8.7 Hz, 2 H), 4.19 (ddd, J = 11.0, 7.7, 3.3 Hz, 1 H), 4.07 (q, J = 6.5 Hz, 1 H), 4.00 (ddd, J = 11.1 , 7.3, 3.5 Hz, 1 H), 3.91 (t, J = 5.7 Hz, 1 H), 3.80 (s, 3 H), 2.32 (br, 1 H), 1.70 (m, 2 H), 1.44 (d, J = 6.6 Hz, 3 H).

The synthetic route of 6298-96-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/76131; (2006); A2;,
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Synthetic Route of 349-65-5,Some common heterocyclic compound, 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, molecular formula is C8H8F3NO, 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.

5-(Trifluoromethyl)-2-methoxyaniline was treated with CDI, followed by 4-(1-oxoisoindolin-5-yloxy)aniline according to Method C2d to afford the urea. Entry 26: 4-Hydroxyacetophenone was reacted with 4-fluoronitrobenzene according to Method A13, Step 1 to give 4-(4-acetylphenoxy)nitrobenzene.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methoxy-5-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; BAYER CORPORATION; US2003/144278; (2003); A1;,
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Synthetic Route of 20469-65-2,Some common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, molecular formula is C8H9BrO2, 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.

In a clean dry round bottom flask, l-bromo-3.5-dimethoxybenzene (8.00 g, 36.9 mmol) was added to 300 ml of dry dichloromethane. The solution was cooled down to 0C and BetaIota (25.00 g, 100 mmol) was added dropwise. After 2 hours, the mixture was allowed to warm to room temperature and stirred over night. Methanol (10 ml) was added dropwise to terminate the reaction. The mixture was poured into water and stirred for 2 hours. Then saturated sodium bicarbonate (100 ml) was added and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, brine and then dried over Na2S04. The residue, after concentration, was purified using chromatography using ethyl acetate/hexane (1:4 v/v) eluent. Yield = 4.39 g (63%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3,5-dimethoxybenzene, its application will become more common.

Reference:
Patent; POLYMEDIX, INC.; UNIVERSITY OF MASSACHUSETTS; LI, Yan; THAKER, Hitesh; TEW, Gregory N.; LIU, Dahui; PAN, Wenxi; WO2013/90185; (2013); A1;,
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Application 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.

A RBF was charged with (1,5-cyclooctadiene)(methoxy)-iridium(i) dimer (0.049 g, 0.075 mmol), 4,4′-di-tert-butyl-2,2′-dipyridyl (0.040 g, 0.149 mmol), and bis(pinacolato)diboron (1.339 g, 5.27 mmol). The flask was flushed with Ar (g), then hexane (15.30 ml) was added. A reflux condenser was attached to the flask, and the flask was heated to 50 C. for 10 minutes. 2-bromo-4-methoxy-1-methylbenzene (2.0 g, 9.95 mmol) was added and the reaction was stirred overnight at 50 C. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 80 g, gradient elution 0-50% EtOAc:Heptane) to afford 2-(4-bromo-2-methoxy-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.694 g, 2.122 mmol, 21.33% yield) as an off-white oily solid. m/z (ESI) 329.1 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-methoxy-1-methylbenzene, its application will become more common.

Reference:
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
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Electric Literature of 592-55-2, 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. 592-55-2, name is 1-Bromo-2-ethoxyethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(A) A mixture of 4-bromo-3-methylphenol (10 g, 53.47 mmol), 1-bromo-2-ethoxyethane (10.62 g, 69.40 mmol) and K2CO3 (11.13 g, 79.95 mmol) in DMF (100 mL) was stirred overnight at 75 C. After cooling to rt, brine (250 mL) was added and the mixture was extracted with EtOAc (4*100 mL). The combined organic extracts were washed with brine (4*100 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. Purification of the resultant residue by silica gel chromatography (5% EtOAc/petroleum ether afforded 1-bromo-4-(2-ethoxyethoxy)-2-methylbenzene (12.25 g, 88%) as light yellow oil which was used directly.

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-ethoxyethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Janssen Pharmaceutica NV; Liang, Yin; Demarest, Keith T.; (109 pag.)US2017/290800; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 592-55-2, name is 1-Bromo-2-ethoxyethane, 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 592-55-2, Recommanded Product: 1-Bromo-2-ethoxyethane

A. 2-Ethoxyethoxynitrobenzene 2-Nitrophenol (91.0 g. 0.65 mole), 2-bromoethyl ethyl ether (100.0 g. 0.65 mole), anhydrous potassium carbonate (9.0 g, 0.72 mole) and acetone (1 liter) were refluxed for 65 hours. The reaction mixture was filtered, and the acetone removed by rotary evaporation. The residue was partitioned between 200 ml. of dichloromethane and 100 ml water. The organic phase was further washed with 200 ml. of 10% sodium hydroxide followed by 100 cc of water. The product (58.0 g) was obtained in 42% yield by a vacuum distillation (100-120 C./0.5 mm).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-ethoxyethane, and friends who are interested can also refer to it.

Reference:
Patent; GAF Corporation; US4178168; (1979); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem