Ethers-buliding-blocks

102-52-3, name is 1,1,3,3-Tetramethoxypropane, 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. category: ethers-buliding-blocks

Stage 5- Preparation of 3-(phenylamino)allylidene)aniline hydrochloride (Bioorg. Med. Chem. 2006, 4, 92-97). Compound having formula (VI) where n=1. 24.7 g of aniline in solution in 300 mL of 0.75 N HCl is added drop by drop to 21.8 g of 1,1,3,3-tetramethoxypropane in solution in 300 mL of 0.75 N HCl. The appearance of an intense orange colour and the precipitation of an orange crystalline solid are observed. The medium is then left under stirring for 3 hours at 50 C. The cooled medium is filtered, vacuum-dried to obtain 15.2 g of orange solid (Yd=44.2%). C15H14N2, HCl-(Mass ESI+400 C. MH+=223.1).

The synthetic route of 102-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS); PIERRE FABRE MEDICAMENT; Guminski, Yves; Imbert, Thierry; Pesnel, Sabrina; Pillon, Arnaud; Le Pape, Alain; Lerondel, Stephanie; US2013/183247; (2013); A1;,
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Reference of 393-15-7,Some common heterocyclic compound, 393-15-7, name is 4-Methoxy-3-(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.

4-Methoxy-3-trifluoromethyl-phenylamine (5 g, 26 mmol) in 12 mL water was cooled to -5 degrees C. (Ice/Methanol bath). Conc. HCl was added dropwise (7 ml), and the reaction mixture was stirred for five minutes. A solution of NaNO2 (2.0 g, 29 mmol) dissolved in 3 ml water was added dropwise over 10 minutes, and the reaction mixture was stirred for 30 min. Sodium acetate (1.8 g, 22 mmol) was then added, and stirring was continued at -5 degrees C. In a separate flask, ethyl alpha-acetoacetate (4.55 g, 29 mmol) in 20 ml absolute ethanol was stirred, and KOH (1.6 g, 29 mmol) dissolved in 3 ml water was added, followed by ice (30 g). The resulting diazonium salt was added quickly to the reaction mixture, rinsing in with 5 ml EtOH, and the reaction mixture was stirred at zero degrees C. for 3.5 hours, then stored at -10 C) for 16 hours. The reaction mixture was warmed to room temperature and extracted with ethyl acetate, washed with brine, and dried over magnesium sulfate. Solvent was removed under reduced pressure to leave a liquid residue. In a separate flask 100 ml EtOH and 21 ml acetyl chloride were mixed, with cooling in an ice bath, then heated to 70 degrees C. The liquid residue was added via pipette over 15 minutes to the acetyl chloride solution. This reaction mixture was heated to reflux for 2.5 hours, cooled, evaporated under reduced pressure. The residue was purified by column chromatography (10% ethyl acetate/hexane) to give 3.0 g 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester, 38% as a white solid and triturated with diethyl ether to give 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester (1.0 g) as a white solid, and 5-Methoxy-3-methyl-4-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester (14%) as a white solid.

The synthetic route of 393-15-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2007/49609; (2007); 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, A new synthetic method of this compound is introduced below., SDS of cas: 22236-10-8

Preparation 9 6-Chloro-N*4*-(4-difluoromethoxyphenyl)-2-methylpyrimidine-4,5-diamine; 4,6-dichloro-2-methyl-pyrimidin-5-ylamine (20.0 g, 110 MoI) was added with stirring to EtOH (80 mL) over 3 minutes to give complete solution. 4-Difluoromethyoxyaniline (18.8 g, 118 MoI) was then added with stirring over 3 minutes. A dark brown solution was observed. EtOH (20 mL) was then added followed by a premixed solution of c.HCI (10 mL) in EtOH (40 mL) at a steady rate over 20 minutes. A slight exotherm up to approx 2O0C was noted. The solution was then warmed to 850C and held at that temperature for 4 hours. The reaction mixture was then cooled to room temperature, and a beige solid precipitated. This reaction mixture was filtered then washed with EtOH (100 ml_) followed by MTBE (3OmL) to remove EtOH traces. The resultant solid was dried in vacuo over the weekend to give the title compound, as the hydrochloride salt, as a beige solid (17.2 g, 45%) 1H NMR (400MHz, CD3OD) delta = 2.55 (s, 3H), 6.89 (t, 1 H), 7.27 (d, 2H), 7.75 (d, 2H) LCMS (System 4) 3.07 mins; m/z (APCI) = 301 [MH+]

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; WO2009/144632; (2009); A1;,
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Ether | (C2H5)2O – PubChem

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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., SDS of cas: 450-88-4

To a mixture of magnesium (0.79 g, 32.5 mmol) and lithium chloride (1.52 g, 35.80 mmol) in THF (33 ml) at room temperature was added 1-bromo-4-fluoro-2-methoxybenzene (3.13 mL, 24.39 mmol) and the reaction was stirred at 70 C for 1.5 hr. The reaction was then cooled to 0 C, and Fe(acac)3 (0.574 g, 1.63 mmol) was added. After 1 minute, allyl chloride (1.33 mL, 16.26 mmol) was added and the reaction was stirred at 0 C for 30 min. The mixture was warmed to room temperature over 1 hr and was heated at 70 C overnight. The reaction was cooled and diluted with petroleum ether (100 mL). The reaction was then quenched by the addition of a saturated NH4Cl solution (100 mL). The mixture was filtered through a Celite pad and the layers were separated. The aqueous layer was extracted with petroleum ether (2 x 100 mL) and the combined organic phases were dried over Na2SO4 and carefully concentrated (25 C, 250 mbar). The residue was purified by Isco chromatography (100% pet ether as the eleuent) to provide (E,Z)-4-fluoro-2- methoxy-1-(prop-1-en-1-yl)benzene (2.25 g, 83 % yield) as a colorless oil. This mixture was approximately a 3:1 mixture of E and Z isomers with a trace of the allyl isomer present. This material was used directly in the next step.1H NMR (400 MHz, CDCl3) delta 7.31 (dd, J = 8.3, 6.8 Hz, 1H), 6.65- 6.53 (m, 3H), 6.14 (dq, J = 15.8, 6.6 Hz, 1H), 3.82 (s, 3H), 1.88 (dd, J = 6.6, 1.7 Hz, 3H).19F NMR (376 MHz, CDCl3) delta -113.30.

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; DOW AGROSCIENCES LLC; BUCHAN, Zachary A.; LU, Yu; JONES, David M.; MEYER, Kevin G.; YAO, Chenglin; (110 pag.)WO2018/44996; (2018); A1;,
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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. 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

To a suspension of NaH (120 g , 3.0 mol) in DMF (1 L) was added dropwise diisopropyl malonate (507 g, 2.7 mol) under an Ar atmosphere, and the reactionwas stirred.Compound 29.2(360 g, 1.35 mol) was then added in portionsand the mixturewas heated to reflux for 48 hr.The reaction mixture was poured into water (2 L), and extracted with PE (6 x 1 L). The combinedorganic layers were dried, filteredand concentrated under reduced pressure 15 to give a yellow oil, which was purified by distillation under reduced pressureto yield compound 29.3 (150 g, 45%) as a colorless oil.

According to the analysis of related databases, 22094-18-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACHAOGEN, INC.; LINSELL, Martin Sheringham; AGGEN, James Bradley; DOZZO, Paola; HILDEBRANDT, Darin James; COHEN, Frederick; KASAR, Ramesh Annasaheb; KANE, Timothy Robert; GLIEDT, Micah James; MCENROE, Glenn A.; WO2014/165075; (2014); A1;,
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Ether | (C2H5)2O – PubChem

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. 59557-91-4, name is 4-Bromo-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 59557-91-4

Intermediate 10 4-Bromo-2-methoxy-N /V-dimethylaniline [00406] Formaldehyde (3.7 mL, 49 mmol, 37% aqueous) and acetic acid (57 uL, 1 mmol) were added to a solution of 4-bromo-2-methoxyaniline (2.0 g, 9.9 mmol) in methanol (10 mL) at 25 C. The mixture was stirred for 2 h, and then sodium cyanoborohydride (3.11 g, 49.5 mmol) was added in portions. The resulting mixture was stirred for 12 h, poured into a saturated NaHC03 solution (40 mL), and then extracted with ethyl acetate (3 x20 mL). The combined organic phases were washed with brine (2×20 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by column chromatography (Si02, petroleum ether/ethyl acetate; 15/1) to give 4-bromo-2-methoxy-N,N-dimethylaniline (2.0 g, 80%) as a brown oil. 1H MR (CDC13): delta 7.02 (dd, 1H), 6.95 (d, 1H), 6.78 (d, 1H), 3.87 (s, 3H), 2.76 (s, 6H); MS: 230.0 [M+H]+.

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 59557-91-4.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (228 pag.)WO2017/49172; (2017); A1;,
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Ether | (C2H5)2O – PubChem

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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Ether | (C2H5)2O – PubChem

Application of 24332-20-5,Some common heterocyclic compound, 24332-20-5, name is 1,1,2-Trimethoxyethane, molecular formula is C5H12O3, 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 3: (E)-5-((5,6-dimethoxypyridin-3-ylimino)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione A round bottom flask was charged with 2-methoxyacetaldehyde dimethyl acetal (2076 mul, 2076 mumol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (299 mg, 2076 mumol). The flask was fitted with a reflux condenser and the mixture was heated at 100 C. for 2 h under nitrogen. 5,6-Dimethoxypyridin-3-amine (320 mg, 2076 mumol) was added, and within a minute a solid had precipitated out of solution. The heterogeneous mixture was heated at 100 C. for 10 min. The mixture was cooled to RT and the solids were filtered and washed with hexanes. (E)-5-((5,6-dimethoxypyridin-3-ylimino)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was isolated as a yellow/orange solid. MS [M+H]=309.

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

Reference:
Patent; CEE, Victor J.; DEAK, Holly L.; DU, Bingfan; GEUNS-MEYER, Stephanie D.; HUA, Zihao; MARTIN, Matthew W.; MARX, Isaac; NGUYEN, Hanh Nho; OLIVIERI, Philip R.; PANTER FABER, Kathleen; ROMERO, Karina; SCHENKEL, Laurie; WHITE, Ryan; US2014/336182; (2014); A1;,
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Ether | (C2H5)2O – PubChem

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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Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 2688-84-8, name is 2-Phenoxyaniline, 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 2688-84-8, category: ethers-buliding-blocks

According to Scheme 34, intermediate 5-a was synthesized:2-Penoxyaniline (25.0, 0.135 mol), 30 ml of hydrochloric acid and 150 ml of water were added to a 1 L round bottom flask reactor, and the mixture was cooled to 0 C and stirred for 1 hour.At the same temperature, 75 ml of an aqueous solution of sodium nitride (11.2 g, 0.162 mol) was added dropwise, followed by stirring for 1 hour.75 ml of an aqueous solution of potassium iodide (44.8 g, 0.270 mol) was added dropwise noting the temperature of the reaction solution not to exceed 5 degrees. After stirring for 5 hours at room temperature, the reaction was completed, washed with sodium thiosulfate aqueous solution and extracted with ethyl acetate and water.The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain Patent; SFC Ltd.; Cha Sun-uk; Jeong Gyeong-seok; Song Ju-man; Lee Yu-rim; Park Sang-u; Kim Hui-dae; Park Seok-bae; (65 pag.)KR2019/111856; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem