Category: ethers-buliding-blocks

Electric Literature of 2339-58-4, 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. 2339-58-4, name is 3-Fluoro-5-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 3-(trifluoromethyl)aniline(5.0 g, 31 mmol) and trimethyl orthoformate (4.9 g, 46.5mmol) was added three drops of sulfuric acid.This mixture was slowly heated to 120 oC to allow MeOH to be distilled off, stirred for 2 h at 120 oC, heated to 170 oCfor 30 min, and cooled to 100 oC.Then aq. HCl (10%; 25 mL) was added.This mixture was then refluxed for 3 h, cooled to 0 oC (ice bath) and finally basified with aq. NaOH (20%).This solution was extracted with EtOAc (3 ¡Á 30 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. The crudeproduct was purified on a silica gel column with gradient elution (hexanes hexane-EtOAc; 1: 10 v/v) to afford S7 as a colorless oil

The synthetic route of 3-Fluoro-5-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Naumiec, Gregory R.; Cai, Lisheng; Pike, Victor W.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 2; (2015); p. 225 – 228;,
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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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H10O2

General procedure: The azido-sugar 2(1 equiv) was dissolved in dry THF (45 mL/mmol) and the required alkyne derivative (5.4 equiv), diisopropylethylamine(1.9 equiv), CuI (0.57 equiv) and DMEDA (5.2 equiv) were added. The reaction mixture was heated to reflux until TLC indicated complete consumption of 2, then the solvent was removed.The residue was dissolved in EtOAc and washed with H2O twice and once with an aqueous solution of EDTA (1%,m/v). The organic layer was dried over MgSO4, filtered and the solvent removed. Purification of the crude material on column chromatography on silica gel (CH2Cl2/EtOAc) afforded the desired product

According to the analysis of related databases, 171290-52-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Van Nguyen, Tai; Hospital, Audrey; Lionne, Corinne; Jordheim, Lars P.; Dumontet, Charles; Perigaud, Christian; Chaloin, Laurent; Peyrottes, Suzanne; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1476 – 1486;,
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Reference of 910251-11-5, 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. 910251-11-5, name is Potassium trifluoro(methoxymethyl)borate belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethyl (R)-l l-chloro-12-(3-hydroxy-3-methylbut-l-yn-l-yl)-3,3- dimethyl-8-oxo-2,3,8,13b-tetrahydro-lH-pyrido[2,l-a]pyrrolo[l,2-c]phthalazine-7-carboxylate (53 mg, 0.093 mmol) was combined with trifluoro(methoxymethyl)-borane, potassium salt (40 mg, 0.26 mmol), Ruphos Pd G2 (5.1 mg, 0.007 mmol), and potassium carbonate (52 mg, 0.37 mmol) in dioxane:water (5: 1, ImL) under argon in a sealed vial. The mixture was stirred at 110 C for 2.5 hours, after which time it was cooled to 50 C and 1M lithium hydroxide (0.19 ml) was added. The mixture was stirred for 90 minutes, then cooled to room temperature, diluted with TFA and acetonitrile, and purified by preparative HPLC to provide (R)-12-(3-hydroxy-3- methylbut- 1 -yn-1 -yl)- 11 -(methoxymethyl)-3,3-dimethyl-8-oxo-2,3,8, 13b-tetrahydro- 1H- pyrido[2,l-a]pyrrolo[l,2-c]phthalazine-7-carboxylic acid as a TFA salt. XH NMR (400 MHz, Acetonitrile-d3) delta 8.47 (s, 1H), 8.01 (s, 1H), 7.50 (d, J = 1.1 Hz, 1H), 7.29 (s, 1H), 4.88 (d, J = 5.9 Hz, 1H), 4.62 (t, J = 0.8 Hz, 2H), 3.47 (s, 3H), 2.60 – 2.43 (m, 2H), 1.94 – 1.86 (m, 1H), 1.67 – 1.60 (m, 1H), 1.58 (s, 6H), 1.37 (s, 3H), 0.63 (s, 3H). iyF NMR (376 MHz, Acetonitrile- d3) delta -77.28 . MS (m/z) 437.2 [M+H]+.

The synthetic route of Potassium trifluoro(methoxymethyl)borate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; CANALES, Eda; CURRIE, Kevin S.; KATO, Darryl; LI, Jiayao; LINK, John O.; METOBO, Samuel E.; SAITO, Roland D.; SCHROEDER, Scott D.; SHAPIRO, Nathan; TSE, Winston C.; WU, Qiaoyin; (262 pag.)WO2018/144605; (2018); A1;,
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Reference of 1836-62-0, 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. 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

d) (3,4-Dihydro-quinazolin-2-yl)-[2-(2-methoxy-phenoxy)-ethyl]-amine 2-(2-Methoxy-phenoxy)-ethylamine (42 mg, 0.25 mmol) was added to a solution of 2-methylsulfanyl-3,4-dihydro-quinazoline hydroiodide (70 mg, 0.23 mmol) in acetonitrile (1 ml), and the mixture was heated overnight (80 C.) in a screw-capped vial. The title compound (42 mg, 62%) was then isolated from the reaction mixture by preparative, reverse-phase HPLC (YMC CombiPrep C18 column 50¡Á20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 6.0 min, lambda=230 nm, flow rate 40 ml/min). MS: m/e=298.2 [M+H+]. 1H NMR (CDCl3): delta 3.71 (3H, s), 3.91 (2H, t), 4.16 (2H, t), 4.57 (2H, s), 6.85-7.01 (8H, m), 7.80 (1H, bs), 8.63 (1H, s).

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-(2-Methoxyphenoxy)ethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Alanine, Alexander; Gobbi, Luca Claudio; Kolczewski, Sabine; Luebbers, Thomas; Peters, Jens-Uwe; Steward, Lucinda; US2006/252779; (2006); A1;,
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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. Formula: C11H15BrO

Reference Example 8 [4-(4-Benzyloxybutoxy)phenyl]methanol The title compound was prepared in a similar manner to that described in Reference Example 6 using benzyl 4-bromobutyl ether instead of benzyl 3-bromopropyl ether. 1H―NMR (CDCl3) delta ppm: 1.52 (1H, t, J=5.6Hz), 1.75-1.95 (4H, m), 3.54 (2H, t, J=6.1Hz), 3.98 (2H, t, J=6.3Hz), 4.52 (2H, s), 4.61 (2H, d, J=5.6Hz), 6.8-6.9 (2H, m), 7.2-7.4 (7H, m)

The synthetic route of ((4-Bromobutoxy)methyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP1548024; (2005); A1;,
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Application of 74137-36-3,Some common heterocyclic compound, 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, molecular formula is C7H6Br2O, 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 250 mL two-necked flask was added 3,5-dibromoanisole (9) (5 g, 18.8 mmol, 1 eq.) Under argon, Anhydrous CH2Cl2 (80 mL) was added, BBr3 (3.5 mL, 37.6 mmol, 2 eq.) Was added dropwise at 0 ¡ã C and maintained at 0 ¡ã C for 3 hours and then allowed to warm to room temperature, The reaction was stopped after darkening for 2 days. The reaction was extracted with CH2Cl2 (50 mL x 3) Combine organic phase, Distilled water (50 mL x 3), Dried over anhydrous magnesium sulfate, The magnesium sulfate was removed by filtration, Steaming the solvent, The residue was purified by silica gel column chromatography (eluent: ether / petroleum ether = 1/9) 4.2 g of a white solid, Yield 90percent. Mp = 86-89 ¡ã C.

The synthetic route of 74137-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Donghua University; Jin, Wusong; Zhang, Dengqing; Xiao, Duoduo; Li, Xianying; Chen, Beihua; Ning, Ruguang; Zhang, Zhen; (13 pag.)CN103819479; (2017); B;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 458-52-6 as follows. Recommanded Product: 2-Fluoro-4-methoxyaniline

A mixture of (+-)-4-[trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl-amino]-2-methylsulfanyl-pyrimidine-5-carbaldehyde (171 mg, 0.46 mmol) (from Example 13a supra), p-toluenesulfonic acid mono-hydrate (10 mg) (Aldrich) and 2-fluoro-4-methoxyaniline (79 mg, 0.56 mmol) (from Example 14a supra) in benzene (30 ML) was refluxed in a Dean-Stark apparatus for 8 hours.The mixture was then cooled and partitioned between ethyl acetate and saturated aqueous potassium carbonate.The organic layer was collected, dried over sodium sulfate, filtered and concentrated.The residue was dissolved in anhydrous tetrahydrofuran (50 ML) and to this solution was added in small portions lithium aluminum hydride (53 mg, 1.40 mmol) (Aldrich) at 0¡ã C. The slurry was allowed to slowly warm up to room temperature and after overnight stirring was poured slowly into a vigorously stirred mixture of ethyl acetate and saturated aqueous potassium sodium tartrate solution.The organic layer was collected, dried over sodium sulfate, filtered and concentrated to a residue that upon purification by silica gel column chromatography with a 0-60percent ethyl acetate in hexanes gradient gave (+-)-[3-trans-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-{5-[(2-fluoro-4-methoxy-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl}-amine as a colorless viscous oil. (Yield 187 mg, 83percent). HRMS m/z calculated for C24H37FN4O2SSi [M+H]+: 493.2464. Found: 493.2472.

According to the analysis of related databases, 458-52-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chen, Yi; Dermatakis, Apostolos; Liu, Jin-Jun; Luk, Kin-Chun; Michoud, Christophe; Rossman, Pamela Loreen; US2004/204427; (2004); A1;,
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Application of 106854-77-7, These common heterocyclic compound, 106854-77-7, name is 1-Bromo-4-(2,2,2-trifluoroethoxy)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.

1-BROMO-4- (2, 2, 2-trifluoroethoxy) benzene (14.5 g, 57 mmol) was dissolved in toluene (250ML) under an argon atmosphere. tert-Butyl PIPERAZINE-1-CARBOXYLATE (12.7 g, 68 mmol), sodium tert-butoxide (7.6 g, 79.5 mmol) rac-2,2′-bis (DIPHENYLPHOSPHINO)-1, 1 -BINAPHTHYL (200 mg, 0.32 mmol) and tris (dibenzylideneacetone) dipalladium (0) (200 mg, 0.2 mmol) were added and the reaction heated to 80 C for 4 hours. The mixture was then cooled and filtered through Celite to yield crude tert-butyl 4- [4- (2, 2,2-trifluoroethoxy) phenyl] piperazine-1- carboxylate (32.47 g). H NMR (400 MHZ, CDC13) : 8 6.90 (4 H, s), 4.30 (2 H, q), 3.60 (4 H, m), 3.05 (4 H, m), 1.45 (9 H, s); 7TL/Z (ES) 305 (MHS- BU).

Statistics shows that 1-Bromo-4-(2,2,2-trifluoroethoxy)benzene is playing an increasingly important role. we look forward to future research findings about 106854-77-7.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/822; (2005); A1;,
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589-10-6, name is (2-Bromoethoxy)benzene, 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. Application In Synthesis of (2-Bromoethoxy)benzene

Cesium carbonate (0.490 g, 1.5 mmol) and 1-(2-bromoethoxy)benzene (0.261 g, 1.30 mmol) were added to a solution of (E)-ethyl 3-(1H-pyrazol-4-yl)acrylate (0.167 g, 1 mmol) in ACN (8 mL) at room temperature. The suspension was stirred overnight at 80 C. The reaction mixture was then cooled down to room temperature and the precipitated solids were filtered off. The filtrate was concentrated and purified by silica gel column chromatography using a gradient of 0-60% of EtOAc in hexanes to provide the title compound (0.203 g, 71%) as a colorless oil. ES+(M+H)+287

The synthetic route of 589-10-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jacques, Vincent; Rusche, James R.; Peet, Norton P.; Singh, Jasbir; US2013/317003; (2013); A1;,
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Electric Literature of 2398-37-0, A common heterocyclic compound, 2398-37-0, name is 1-Bromo-3-methoxybenzene, molecular formula is C7H7BrO, 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.

The advantageous effect of adding zinc chloride to an amination reaction was demonstrated in the amination reaction of 3-bromoanisole. the results of which are summarized in Table 10. When 3-bromoanisole was reacted under the standard lithium amide amination conditions, using lithium amide (10 eq.) in the presence of (CyPF-^-Bu)PdCl2 (1 mol%) in DME gave a complicated mixture of products was obtained (Table 10, Entry 1). When conducted in the presence of zinc chloride and TMEDA, however, the reaction could successfully gave the desired monoarylation product, 3-methoxyaniline, although at high concentrationsN,N-dimethyl-3-methoxyaniline was formed in a significant amount as a by- product (Table 10, Entries 3 and 4). Under optimized conditions (Table 10, Entries 8 and 9), 3-methoxyaniline was formed selectively in good yield.

The synthetic route of 2398-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YALE UNIVERSITY; WO2007/109365; (2007); A2;,
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