Category: ethers-buliding-blocks

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. 4698-11-7, name is 10-Methoxy-5H-dibenzo[b,f]azepine, A new synthetic method of this compound is introduced below., Formula: C15H13NO

10-Methoxy-5H-dibenzo[b,f]azepine 4 (500 g, 2.23 mol) and isopropanol (1.0 L) were charged into a round bottomed flask and stirred for 5-10 min. 50% Aqueous hydrochloride solution (250 mL) was then added slowly to the mixture at 25-35 ?C and stirred for 15 min. The reaction mixture was heated to 60-65 ?C and maintained for 2-3 h. The progress of the reaction was monitored by TLC, and after completion of the reaction (by TLC), ethyl acetate (1.5 L) and water (1.0 L) were added into the reaction mixture and stirred for 5-10 min. Organic layer was separated and the aqueous layer was extracted with ethyl acetate (1.5 L). The combined organic layer was washed with 5% caustic lye solution (500 mL) followed by 10 % NaCl solution (500 mL) and evaporated at 50-55?C under reduced pressure. n-Hexane (500 mL) was then added into the crude product at 25-30 ?C and stirred for 1-2 h. The obtained solid was collected by filtration, washed with n-hexane (250 mL) and dried at 60-65 ?C to afford the title compound 6 as yellow solid (400 g) in 85.4% yield and >98.2% purity. Spectroscopic data were found to be in agreement with the data collected from authentic sample of intermediate 6. IR (KBR): 3329, 3284, 3040, 1643, 1474, 1309, 753 cm-1; 1H NMR (400 MHz, CDCl3): delta 3.72 (2H, s), 6.78-7.91 (8H, m); 13C NMR (400 MHz, CDCl3): delta 49.4, 119.1, 119.2, 119.8, 124.1, 124.5, 127.7, 127.9, 129.8, 130.3, 133.7, 141.5, 146.8, 190.1; HRMS calcd for C14H11NO, 210.0919; found 210.0909.

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:
Article; Ravinder; Rajeshwar Reddy; Sridhar; Murali Mohan; Srinivas, Katkam; Panasa Reddy; Bandichhor, Rakeshwar; Tetrahedron Letters; vol. 54; 22; (2013); p. 2841 – 2844;,
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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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H13NO2

To a solution of 5-fluoro-2-nitrobenzoic acid (6.6g, 35.66 mmol) in dichloromethane (100 mL) were added DIPEA (9.22 g, 71.3 mmol), HOBt (6.0 g, 39.2 mmol) and EDCI (10.2 g, 53.5 mmol). After about 15 min stirring, to the reaction mixture was added a solution of 2,4-dimethoxybenzyl amine (5.96 g, 35.66 mmol) in dichloromethane (50 mL) dropwise under nitrogen atmosphere. The resulting mixture was stirred under nitrogen atmosphere at room temperature for 16 h. The reaction mixture was washed successively with 1N HC1 (100 mL), sat. NaHCCb (100 mL) and brine (100 mL). The organic phase was then dried over MgS04. Filtration and solvent removal in vacuo afforded a yellowish solid, wt: 9.3g (78%). MS: [M+l] = 335.

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 20781-20-8.

Reference:
Patent; AGENEBIO, INC.; MEKONNEN, Belew; BUTERA, John, A.; HUANG, Jianxing; PATEL, Hemantbhai; JIANG, Qin; HERR, Robert, Jason; MAYHEW, Nicholas, James; FREEMAN, Emily, Elizabeth; (682 pag.)WO2019/246300; (2019); A1;,
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Synthetic Route 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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These common heterocyclic compound, 41406-00-2, name is 3-Isopropoxyaniline, 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: C9H13NO

Thiophosgene (46 muL, 0.60 mmol) was added dropwise to a stirred solution of 3- isopropoxy aniline (82 mg, 0.543 mmol) and calcium carbonate (272 mg, 2.72 mmol) in DCM/H2O (1 : 1) (4 mL). This was stirred at room temperature for 1 h. The phases were separated and the organic layer was dried and concentrated in vacuo. The residue was dissolved in DMF (3 mL) and added to a stirred solution of N-[4-(4-acetylpiperazin-l- yl)phenyl]-2-hydrazino-2-oxoacetamide (Intermediate 21, 100 mg, 0.33 mmol) in DMF at 850C. This mixture was stirred at 850C for 1 h then EDAC (105 mg, 0.54 mmol) was added. The mixture was stirred at 1000C for a further 1 h then allowed to cool and treated with H2O (10 mL). The resulting precipitate was filtered and washed sequentially with DMSQ/MeCN/H2O (7:2:1) (5 mL) and ether (5 mL) to give the title compound as a white solid (12 mg, 8%); 1HNMR delta 10.90 (IH, s), 10.82 (s, IH), 7.67 (2H, d), 7.25 (2H, d), 7.10 (IH, d), 6.97 (2H5 d), 6.63 (IH, d), 4.59 (IH, m), 3.58 (4H, br. s), 3.15 (2H, m), 3.09 (2H, m), 2.04 (3H, s), 1.32 (3H, s), 1.30 (3H5 s); MS m/e MH+ 465.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/64189; (2006); A1;,
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Synthetic Route of 202865-80-3, 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. 202865-80-3, name is 4-Bromo-2-fluoro-1-isopropoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Potassium acetate ( 10.52 g, 107.2 mmol) and bis(pinacolato)diboron ( 15g, 58.96 mmol) were added to a solution of intermediate 11 ( 10.52 g, 107.2 mmol) in dioxane ( 125 ml), and the solution was degassed for 30 min. [1, 1 ‘- Bis(diphenylphosphino)ferrocene]dichloro palladium(II).CH2Cl2 (4.4g, 5.36 mmol) was added under nitrogen atmosphere and heated to 80C. After 12h the reaction mixture was filtered through celite and concentrated. The crude product was purified by column chromatography with ethyl acetate: petroleum ether to afford the title compound as a yellow oil ( 13.9g, 99%) which was used without purification in the next step.

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

Reference:
Patent; RHIZEN PHARMACEUTICALS SA; NAGARATHNAM, Dhanapalan; VAKKALANKA, Swaroop Kumar, V.S.; MUTHUPPALANIAPPAN, Meyyappan; VISWANADHA, Srikant; BABU, Govindarajulu; BHAVAR, Prashant, Kashinath; WO2012/151525; (2012); A1;,
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Synthetic Route of 2688-84-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2688-84-8 name is 2-Phenoxyaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

In a 50L double-layer cryostat equipped with mechanical stirring, 5 kg was added (due to batch reaction,A plurality of reactors are simultaneously carried out, so that the amount of the raw materials is sufficient to meet the requirements of the step. 2-Aminodiphenyl ether prepared in the above step (2), 30 L of acetonitrile, and the temperature in the autoclave is lowered to -10 C.4.80 Kg of N-bromosuccinimide was added in three portions, and the reaction was carried out for 2 hours.The mixture is distilled to recover acetonitrile, and then 15 L of water is added to the concentrate.15 L of dichloromethane, stirred and separated, and the organic phase was distilled to recover dichloromethane.Drying again gave a brown solid of 7.06Kg.The product was identified as 1-amino-5-bromodiphenyl ether by 1H-NMR and 13C-NMR.The yield was 99%, and the purity of the product was 98% by liquid chromatography.

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

Reference:
Patent; Xinxiang Runyu New Materials Technology Co., Ltd.; Geng Weizhi; Zhou Yi; Li Heng; Zhang Yinlong; Ma Chenyang; (18 pag.)CN109942527; (2019); A;,
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Reference of 171290-52-1, 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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Azide 13 (300 mumol), alkyne (750 mumol), CuSO4 (9.6 mg, 60 mumol) and sodium ascorbate (60.0 mg, 300 mumol) were dissolved in 1:1 t-BuOH/H2O (3 mL). The mixture was stirred for 2 h at rt. After the completion of the reaction, the mixture was filtered and washed with H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 * 70 mL). The combined organic extracts were dried over anhyd MgSO4, filtered, and concentrated by rotary evaporation (residue B). The solid A and residue B were combined and purified by column chromatography to afford 8 or 9.

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

Reference:
Article; Song, Doohee; Park, Yunjeong; Yoon, Jieun; Aman, Waqar; Hah, Jung-Mi; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4855 – 4866;,
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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. 41365-75-7, name is 1-Amino-3,3-diethoxypropane, A new synthetic method of this compound is introduced below., Recommanded Product: 41365-75-7

j00273J To a solution of [(R)-(4-chlorophenyl)-[(25,3 S,4R, 5R)-5-(4-chloropyrrolo[2,3 – d]pyrimidin-7-yl)-3 ,4-dihydroxy-tetrahydrofuran-2-yl]methyl] 4-phenylbenzoate (Int-3) (400 .mg,0.69 mmol) in Ethanol (2 mL), 3,3-diethoxypropan-1-amine (2.mL, 12.36 mmol) was added. The mixture was stirred at 80 C for 4 h. LCMS indicated the reaction was completed and formation of the mixture of 22a. The mixture of crude products was used directly for the next step.:_1002741 To the reaction mixture of compound 22a (both [(R)-(4-chlorophenyl)- [(2S,3 S,4R,5R)-5-[4-(3 ,3 -diethoxypropylamino)pyrrolo[2,3 -d]pyrimidin-7-yl]-3 ,4-dihydroxy- tetrahydrofuran-2-yl]methyl] 4-phenylbenzoate (4.mL, 0.16 mmol) and (2R,3 S,4R,5R)-2-[(R)-(4- chlorophenyl)-hydroxy-methyl] -5 -[4-(3 ,3 -diethoxypropylamino)pyrrolo[2, 3 -d]pyrimidin-7- yl]tetrahydrofuran-3 ,4-diol (4 .mL, 0.53 mmol) was contained), hydrazine hydrate (2. mL, 41.15 mmol) was added. The mixture was stirred at 25 C for 4 h. The mixture was purified by reverse phase Chem-flash eluting with CH3CN/H20 from 10/90 to 90/10 to give (2R,35,4R,5R)-2-[(R)-(4- chlorophenyl)-hydroxy-methyl] -5 -[4-(3 ,3 -diethoxypropylamino)pyrrolo[2, 3 -d]pyrimidin-7-yl]tetrahydrofuran-3,4-diol (22b) (297 mg, 0.557 mmol, 85.2% yield) (total yield over two steps) as a yellow solid. LCMS M+H: 507.1

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; PRELUDE THERAPEUTICS, INCORPORATED; LUENGO, Juan; LEAL, Raul, A.; LIN, Hong; SHETTY, Rupa; (153 pag.)WO2018/152501; (2018); 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. 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2,6-Difluoro-3,5-dimethoxyaniline

To a solution of the 7.00 g (33.4 mmol) of 4-cyclopropylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde in 500 mL of toluene was added 6.33 g ( 33.4 mmol, 1 equivalent) of 2,6-difluoro-3,5-dimethoxy-phenylamine and 1.94 g (8.36 mmol, 0.25 equivalents) of camphorsulfonic acid. The reaction was warmed to reflux and the formed water was removed with the aid of a Dean-Stark trap. After reacting for 48 hours, the reaction was concentrated in vacuo. The residue was stirred with ether and filtered. The filter pad was dissolved in dichloromethane, stirred with silica gel, and concentrated in vacuo. The residue was placed in the sample injection module of a Biotage FLASH 75 chromatographic apparatus. Chromatography of the crude material down a Biotage 500 g silica gel column with 2:1 hexane/ethyl acetate, then 1:1 hexane/ethyl acetate and finally 9:1 ethyl acetate/ethanol gave 8.92 g (70%) of title compound as a solid: mp 172 C.-174 C. MS (APCI) (m+1)/z 381.0 Analysis calculated for C17H18aF2N4SO2: C, 53.67; H, 4.77; N, 14.73. Found: C, 53.54; H, 4.58; N, 14.61.

The synthetic route of 651734-54-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chivikas Connolly, Cleo J.; Deur, Christopher James; Hamby, James Marino; Hoyer, Denton Wade; Limberakis, Chris; Reed, Jessica Elizabeth; Schroeder, Mel Conrad; Taylor, Clarke; US2004/19210; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 116557-46-1, name is 3-Bromo-2-methoxyaniline, 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 116557-46-1, Recommanded Product: 116557-46-1

[00239] 3-Bromo-2-methoxyaniline (500 mg, 2.47 mmol), bis(pinacolato)diboron (755 mg,2.97 mmol) and potassium acetate (728 mg, 7.42 mmol) were mixed in 1,4-dioxane (8 mL) and nitrogen gas was blown through for 5 minutes. 1,1-Bis(diphenyl-phosphino)ferrocene- palladium(ll)dichloride DCM adduct (173 mg, 0.21 mmol) was added and nitrogen blown through again. The mixture was heated under reflux conditions for 2.5 hours then allowed to cool (black mixture). Dl water and DCM were added (35mls of each) and the mixture wasstirred vigourously for 30 minutes then passed through a hydrophobic frit. The DCM phase was concentrated down to remove excess Dioxane then redissolved in minimum DCM and was purified by flash chromatography eluting with 0-100% ethyl acetate/isohexane over 40 minutes. Product containing fractions were concentrated down to give 2-methoxy-3-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)aniline as an off-white solid 358mg. [00240] 1H NMR (DMSO-d6): O 6.88 (m, 3H), 4.80 (bs, 2H), 3.64 (5, 3H), 1.29 (5, 12H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-2-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; GOLDBERG, Kristin; HAMILTON, Niall; JONES, Stuart; JORDAN, Allan; LYONS, Amanda; NEWTON, Rebecca; OGILVIE, Donald; WASZKOWYCZ, Bohdan; WO2015/79251; (2015); A1;,
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