Category: ethers-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 35822-58-3, name is 2-Bromobenzaldehyde diethyl acetal, 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 35822-58-3, Formula: C11H15BrO2

To a solution of aryl bromide (1.94 g, 7.49 mmol, 1.0 equiv) in THF (20 mL) at -78 C under N2 was added 1.5 M n-BuLi in hexanes (7.49 mL, 11.2 mmol, 1.5 equiv). After 30 mm DMF (869 iL, 11.2 mmol, 1.5 equiv) was added. The mixture was slowly warmed to r.t. over 4 h, at which time it was quenched with sat. aq. NH4C1 (40 mL) and extracted with EtOAc (3 x 20 mL). The organics were dried over Na2SO4, filtered and concentrated in vacuo. The resultant oil was purified by flash chromatography on silica gel (95:4:1 hexanes/EtOAc/Et3N) to yield the product (2.105 g, 87%) as a yellow oil. R1= 0.46 (3:1 hexanes/EtOAc). The analytical data match those previously reported: Ueda, M.; Kawai, S.; Hayashi, M.; Naito, T.; Miyata., 0. 1 Org. Chem. 2010, 75, 914.

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; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; SALK INSTITUTE FOR BIOLOGICAL STUDIES; PACHE, Lars; CHANDA, Sumit, K.; VAMOS, Mitchell, Dennis; COSFORD, Nicholas David, Peter; TERIETE, Peter; MARLETT, John; DIAZ, Arturo; YOUNG, John, A.T.; WO2015/187998; (2015); A2;,
Ether – Wikipedia,
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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-(4-Methoxyphenyl)ethylamine

To a solution of [3-(3,5-Dimethoxy-phenyl)-1 ,4-dimethyl-1 H-pyrazolo[3,4-b]pyridin-6-yloxy]- acetic acid (building block A1 , 100 mg, 0.28 mmol) in CH2CI2 were added HOBt x H20 (64 mg, 0.42 mmol), EDC x HCI (80 mg, 0.42 mmol) and NEt3 (0.12 ml, 0.84 mmol). After stirring at rt for 5 min, (S)-1-(4-methoxyphenyl)ethanamine (64 mg, 0.42 mmol) was added andstirring continued for 18 h. Then, water was added and the mixture extracted 3 times withDCM. The organic phases were dried over Na2S04 and the solvent removed under reduced pressure. Purification by reverse phase HPLC (Sunfire C18 OBD column) followed byliberation of the free base (SPE cartridge SCX-1 , eluent 7M NH3 in methanol) yielded the title compound (17 mg, 12%). [1 H-NMR (DMSO-d6, 600 MHz) delta 8.48 (d, 1 H), 7.21 (d, 2H),6.82 (d, 2H), 6.70 (s, 1 H), 6.58 (s, 1 H), 5.00-4.88 (m, 1 H), 4.87 (d, 1 H), 4.83 (d, 1 H), 3.85 (s, 3H), 3.78 (s, 6H), 3.70 (s, 3H), 2.37 (s, 3H), 1.37 (d, 3H); UPLC-MS Rtj = 1.14 min; [M+H]+ = 491.2]

According to the analysis of related databases, 6298-96-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BADIGER, Sangamesch; BEHNKE, Dirk; BETSCHART, Claudia; CHAUDHARI, Vinod; CHEBROLU, Murali; COSTESTA, Simona; HINTERMANN, Samuel; MEYER, Arndt; PANDIT, Chetan; WO2011/76744; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 54314-84-0, name is ((3-Bromopropoxy)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 54314-84-0, COA of Formula: C10H13BrO

(Step 3) {1-[1-(1-Tert-butyloxycarbonyl)piperidin-4-yl] imidazolidin-2-ylidene}malononitrile (3.68 g, 11.59 mmol) obtained in the Step 2 was dissolved in DMF (25 mL) and the solution was added with potassium carbonate (3.20 g, 23.18 mmol) and benzyl-3-bromopropylether (2.46 mL, 13.91 mmol), followed by stirring at 80°C for 6.5 hours. Further, the mixture was added with potassium carbonate (1.60 g, 11.59 mmol) and benzyl-3-bromopropylether (1.72 mL, 5.80 mmol), followed by stirring at 80°C for 14.5 hours. The mixture was added with saturated brine and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform to chloroform/methanol (20:1)) to obtain {3-(3-benzyloxypropyl)-1-[1-(1-tert-butyloxycarbonyl)piperidin-4-yl]imidazolidin-2-ylidene} malononitrile (4.84 g, 89.6 percent) as a white solid. 1H NMR (CDCl3, deltappm): 1.45 (s, 9H), 1.49-1.56 (m, 2H), 1.74-1.79 (m, 2H), 1.94-2.04 (m, 2H), 2.81 (brt, J = 12.3 Hz, 2H), 3.38-3.45 (m, 2H), 3.52-3.60 (m, 4H), 3.69 (t, J = 7.1 Hz, 2H), 4.18-4.35 (m, 3H), 4.49 (s, 2H), 7.26-7.38 (m, 5H).

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, ((3-Bromopropoxy)methyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1847530; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 93919-56-3,Some common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, 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.

General procedure: To a solution of 4 (290mg, 1.02mmol) in DMF (1.5mL), CDI (198mg, 1.23mmol) was added under N2 protection. The resulting reaction was stirred 50C. After 2h, the mixture was cooled to room temperature, and the corresponding benzylamine (1.53mmol) was added. The resulting reaction was stirred 50C under N2 protection overnight. Then the mixture was cooled to room temperature, quenched with 1M hydrochloric acid, diluted with water (50mL), and extracted with CH2Cl2 (60mL×3). The combined organic layer were washed with saturated solution of NaCl (60mL×3), dried over MgSO4, concentrated and purified by flash chromatography eluting with 5-50% ethyl acetate in petroleum ether, to provide the desired products 5a-5d.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (4-(Trifluoromethoxy)phenyl)methanamine, its application will become more common.

Reference:
Article; Liu, Siming; Jiang, Ying; Yan, Ruohong; Li, Zhonghuang; Wan, Shanhe; Zhang, Tingting; Wu, Xiaoyun; Hou, Ju; Zhu, Zhengguang; Tian, Yuanxin; Zhang, Jiajie; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 358 – 375;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 2398-37-0, 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 2398-37-0 as follows.

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.

According to the analysis of related databases, 2398-37-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YALE UNIVERSITY; WO2007/109365; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 51388-20-6, name is 4-(Benzyloxy)aniline hydrochloride, 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. name: 4-(Benzyloxy)aniline hydrochloride

A solution of Ethyl 2-Acetyl-4- (2, 4-dichlorophenyl)-4-oxobutanoate from Exl, Step A (2.85 g, 9.0 mmol) and 4-benzyloxyaniline hydrochloride (2.14 g, 9.1 mmol) in 1: 1 ethanol/acetic acid (80 mL) was heated at reflux for 18h. After cooling, the solution was partially concentrated and diluted with ethyl acetate. It was washed with saturated NaHC03 solution, and the organic layer was dried (MgS04) and concentrated. The residue was purified by flash column chromatography (10: 1 hexanes/EtOAc) to afford the title compound as a white solid (1.67 g, 39%) :’H NMR (300 MHz, CDC13) 8 6.90-7. 40 (m, 12H), 6.73 (s, 1H), 5.02 (s, 2H), 4.31 (q, J= 7.1 Hz, 2H), 2.40 (s, 3H), 1.36 (t, J= 7.1 Hz); ESI MS m/z 480 [C27H23Cl2NO3 + H] + ; HPLC (Method A) 99.6% (AUC), {R = 36.2 min.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/80328; (2005); A1;,
Ether – Wikipedia,
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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, A new synthetic method of this compound is introduced below., Product Details of 6298-96-0

General procedure: The appropriate amine derivative was dissolved in the appropriate solvent (ethanol or pyridine) after which CS2 was added. The mixture was refluxed overnight under N2. Next, the solution was concentrated by evaporating the solvent and then cooled to give aprecipitate. The precipitated product was isolated by vacuum filtration. The crude N,N’-bis-thiourea was purified by recrystallizationfrom ethanol.

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; Tuncel, Senel Teke; Gunal, Sule Erol; Ekizoglu, Melike; Gokhan Kelekci, Nesrin; Erdem, Safiye S.; Bulak, Ece; Frey, Wolfgang; Dogan, Ilknur; Journal of Molecular Structure; vol. 1179; (2019); p. 40 – 56;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 767-91-9, These common heterocyclic compound, 767-91-9, name is 2′-Methoxyphenyl acetylene, 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.

b) 2-Isopropoxy-5-(2-methoxy-phenylethynyl)-benzoic acid methyl ester; 5-lodo-2-isopropoxy-benzoic acid methyl ester (500 mg), 2-methoxy-phenyl acetylene (0.40 ml), palladium dichlorobis(triphenylphosphine) (12 mg) and Cul (6 mg) in diethylamine (10 ml) were stirred at 60C for 12 hours. The reaction mixture was concentrated and extracted with ethylacetate / water. The combined organic layers were dried over sodium sulphate and the solvent was evaporated. The title compound was obtained in 64 % yield after flash chromatography. 1H-NMR (CDCl3): 7.97 d (J = 2.3 Hz, 1 H); 7.59 dd (J = 2.3 Hz /8.7 Hz, 1 H); 7.47 dd (J = 7.5 Hz /1.7 Hz, 1 H); 7.30 m (1 H); 6.96 m (3H); 4.62 m (1 H); 3.91 s (3H); 3.88 s (3H); 1.38 d (J =8.7 Hz, 6H).

The synthetic route of 767-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1975159; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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. Product Details of 19056-40-7

To a solution of 4-bromo-3-(methoxymethyl)aniline (0.6 g, 2.78 mmol) andpotassium phosphate tribasic (0.295 g, 1.39 mmol) in acetonitrile (25 mL) at 0 °C, was added 2,4-dibromobutyryl chloride (0.88 g, 3.33 mmol) dropwise. The reaction mixturewas warmed to rt and stirred for 1 h. NaOH (0.6 g, 15.0 mmol) (in 1.2 mL water, 50percentaqueous solution) was added to the reaction mixture, which was stirred at rt for 3 h. The reaction mixture was filtered, the solid was rinsed with acetonitrile, and the filtrate was concentrated. The crude product was purified by flash chromatography (eluting with 20- 30percent EtOAc in hexane) to give 3-bromo-1-(4-bromo-3-(methoxymethyl)phenyl)pyrrolidin-2-one (0.71 g, 70percent yield) as a pale brown oil. MS(ESI) m/z: 363.8 (M+H) ?HNMR (300 MHz, chloroform-d) oe ppm 7.69 – 7.64 (m, 1 H), 7.63 – 7.60 (m, 1 H), 7.57 -7.53 (m, 1 H), 4.59 (dd, J6.8, 3.0 Hz, 1 H), 4.52 (s, 2 H), 4.12 -4.01 (m, 1 H), 3.90 -3.79 (m, 1 H), 3.50 (s, 3 H), 2.80 – 2.67 (m, 1 H), 2.55 – 2.41 (m, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19056-40-7, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GLUNZ, Peter W.; SITKOFF, Doree F.; BODAS, Mandar Shrikrishna; YADAV, Navnath Dnyanoba; PATIL, Sharanabasappa; RAO, Prasanna Savanor Maddu; THIYAGARAJAN, Kamalraj; MAISHAL, Tarun Kumar; (498 pag.)WO2016/144936; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene, molecular formula is C9H11BrO, 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. Recommanded Product: 36449-75-9

b) At rt, a solution of 1-(2-bromo-ethyl)-2-methoxy-benzene (1.0 g, 4.15 mmol) inabs. THF (5 mL) is added to Mg turnings (0.13 g, 5.35 mmol) suspended in abs.THF (5 ml) over a period of 20 min. The thus obtained Grignard reagent is then added at to an ice-cold solution of (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid methoxy-methyl-amide (400 mg, 1.5 mmol) in THF (5 ml). The reaction mixture is stirred at rt for 1 h, quenched by adding sat. aq. NhUCI (10 ml_), diluted with water (100 ml) and extracted twice with DCM (100 ml_). The combined organic extracts are dried over NaaSO/j, filtered and evaporated . The resulting residue is purified by prep. HPLC to afford 3-(2-methoxy-phenyl)-1-((1aS,5aR)-1,1,2~trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]penta-len-4-yl)-propan-1-one (390 mg) as a colourless oil. LC-MS: tR = 1.15 min, [M+1f = 341.21; 1H NMR (CDCI3): 8 7.22-7.14 (m, 2H), 6.90-6.81 (m, 2H), 3.82 (s, 3H), 3.20-2.90 (m, 5H), 2.79 (d, J = 18.8 Hz, 1H), 2.38 (s, 3H), 1.88 (d, J = 2.9 Hz, 2H), 1.12 (s, 3H), 0.72 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36449-75-9, its application will become more common.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; WO2006/10379; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem