Category: ethers-buliding-blocks

Application of 175278-17-8, 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. 175278-17-8 name is 2-Bromo-4-(trifluoromethoxy)aniline, 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.

A solution of commercially available 2-bromo-4-(trifluoromethoxy)aniline (theproduct of step 1, Example 55, 4.00 g, 15.63 mmol) in DMF (1 0 mL) was addedslowly to a suspension of NaH (60% in mineral oil, 1.13 g, 46.88 mmol) in DMF(20 mL) at 0C. After warming to room temperature the reaction mixture wasstirred for 30 minutes. Commercially available tert-butyl 4-(chloromethyl)-5,6-dihydropyridine-1 (2H)-carboxylate (3.62 g, 15.63 mmol) in DMF (1 0 mL) was added and the mixture stirred at room temperature for 1 hour. Cold water (100 mL) was added and the mixture extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with cold water (2 x 50 mL) and brine(5OmL), dried over anhydrous sodium sulphate and concentrated. The crudematerial was purified by flash chromatography eluting with 20% ethylacetate/hexane to afford the title compound as grey solid (2.5 g, 36%): 1 H NMR(400 MHz, DMSO-d6) oe: 1 .38 (5, 9 H), 1 .99 (bs, 2 H), 3.39 (t, 2 H), 3.75 (bs, 4 H),5.50 (5, 1 H), 5.79 (t, 1 H), 6.60 (d, 1 H), 7.17 (d, 1 H), 7.47 (d, 1 H). LC-Ms(m/z): [M-H] = 448.8.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-4-(trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; ZOETIS SERVICES LLC; WENDT, John; COX, Mark; SHEEHAN, Susan, M.k.; CURTIS, Michael, P.; RESPONDEK, Tomasz; EWIN, Richard, Andrew; KYNE, Graham, M.; JOHNSON, Paul, D.; WO2015/100232; (2015); A2;,
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Application of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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-1: To a stirred solution of methyl 2-oxo-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-6-carboxylate (0.18 g, 0.9366 mmol) in acetic anhydride (4 ml) was added triethyl orthobenzoate (0.630 g, 2.8098 mmol) at RT and the mixture was refluxed for 3 h at 110° C. The reaction mixture was evaporated and the resulting residue was used as such into next step without purification. [0212] Step-2: To a stirred solution of product from step-1 (0.18 g) in DMF (4 ml) was added N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide (0.180 g, 0.6861 mmol) at RT and the reaction mixture was heated at 110° C. for 1 h. The reaction mixture was cooled to RT and stirred with triethyl amine (1 ml) for half an hour. The reaction mixture was evaporated and the crude product was purified by column chromatography using 0 to 10percent methanol in dichloromethane as eluent to afford (Z)-methyl 1-acetyl-3-((4-(N-methyl-2-(4-methylpiperazin-1-yl) acetamido)phenylamino)(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-6-carboxylate as yellow solid. MS (ES+): m/z 583.4 (MH+).

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANGION BIOMEDICA CORP.; NARAYAN, Prakash; HUANG, Brian; PAKA, Prani; PAKA, Latha; GOLDBERG, Itzhak D.; US2015/105380; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4393-09-3, name is (2,3-Dimethoxyphenyl)methanamine, 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 4393-09-3, Computed Properties of C9H13NO2

Step 4 Preparation of 5-cyano-N-(2,3-dimethoxybenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide To a solution of methyl 8-(benzoyloxy)-5-cyano-1,6-naphthyridine-7-carboxylate (264 mg, 0.792 mmol) in anhydrous toluene (12 ml) was added 2,3-dimethoxybenzyl amine (132 mg, 0.79 mmol) and the solution was stirred at reflux under argon overnight. The solvent was removed under reduced pressure to give a brown syrup which was subsequently taken up into ether (10 ml). After stirring for 4 hours the solids were collected by vacuum filtration and dried overnight on an aberhalden to give an off white solid. 1H NMR (CDCl3, 400 MHz) delta 9.26 (1H, d, J=2.8 Hz), 8.59-8.56 (1H, d, J=8.5 Hz), 8.39 (1H, b), 7.82-7.79 (1H, dd, J=4.2 and 8.5 Hz), 7.07 (1H, t, J=7.9 Hz), 6.98 (1H, d, J=6.6 Hz), 6.93 (1H, d, J=8.2 Hz), 4.72 (2H, d, J=6.0 Hz), 3.97 (3H, s) and 3.89(3H, s) ppm.

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

Reference:
Patent; Anthony, Neville J.; Gomez, Robert P.; Young, Steven D.; Egbertson, Melissa; Wai, John S.; Zhuang, Linghang; Embrey, Mark; Tran, LeKhanh; Melamed, Jeffrey Y.; Langford, H. Marie; Guare, James P.; Fisher, Thorsten E.; Jolly, Samson M.; Kuo, Michelle S.; Perlow, Debra S.; Bennett, Jennifer J.; Funk, Timothy W.; US2003/55071; (2003); A1;,
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Electric Literature of 22094-18-4, 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.

Diisopropyl malonate (72 g, 0.38 mol) was added dropwise, under nitrogen, to a stirred suspension of sodium hydride (17 g, 0.42 mol) in dry N,N-dimethylformamide (140 mL, 1.8 mol) at a rate such that the temperature was maintained below 70 C. On cessation of hydrogen evolution, 1,3-dibromo-2,2-dimethoxypropane (50 g, 0.2 mol) was added in one portion and the mixture heated at 140 C. for 48 h. The cooled mixture was poured into sat. solution of ammonium chloride (300 mL), extracted with hexane. The organic layer was washed with sat. sodium bicarbonate, brine, dried over sodium sulfate, and evaporated to dryness. The residue was distilled under vacuum (oil pump) to afford the desired cyclobutane compound (31 g, 56.32%). bp 92-94 C./0.01 mm). 1H NMR (400 MHz, CDCl3): delta 5.02 (2H, sept., J=6.4 Hz), 3.12 (6H, s), 2.66 (4H, s), 1.11 (12H, d, J=6.4 Hz.) ppm.

The chemical industry reduces the impact on the environment during synthesis 1,3-Dibromo-2,2-dimethoxypropane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; INCYTE CORPORATION; US2009/233903; (2009); 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. 16618-68-1, name is 3-Bromo-5-methoxyaniline, A new synthetic method of this compound is introduced below., COA of Formula: C7H8BrNO

Step 1 : 4.0g (0.02 mol) of 3-Bromo-5-methoxy-aniline, 4.6 g (0.05 mol) of glycerol, 2.46g (0.02 mol) of nitrobenzene and 12 ml of 75% sulfuric acid were stirred for 3 h at 150C. After this dark solution was poured onto 100 g of crushed ice, 100 ml of ethylacetate (EtOAc) and 30 ml of 30% solution of NaOH. After 1 hour brown solid was filtered off and the organic layer was separated. After filtering through Si02 and evaporation of solvent 7-bromo-5- methoxy-quinoline and 5-bromo-7-methoxy-quinoline were separated as mixture approximately 60:40 (total 3.5g, 74%) This mixture was separated to individual 7-bromo-5- methoxy-quinoline and 5-bromo-7-methoxy-quinoline with column chromatography on silica-gel with benzene-EtOAc (3: 1) as eluent. Yield of pure 7-bromo-5-methoxy-quinoline was 950 mg (27% from mixture).

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KLICIC, Jasna; SCHAENZLE, Gerhard; WOLLIN, Stefan Ludwig Michael; CONVERS-REIGNIER, Serge Gaston; EAST, Stephen Peter; MARLIN, Frederic Jacques; MCCARTHY, Clive; SCOTT, John; WO2013/14060; (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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-2-(2-bromoethoxy)ethane

Compound 2b (100 mg) was reacted with bis(2-bromoethyl) ether(1.0 mL) in MeCN (10 mL) in the presence of K2CO3 (25 mg) and 18-crown-6-ether (7.4 mg) at 50 C for 5 h. Next, the reaction mixture was concentrated on a rotary evaporator and then poured into hexane to remove any unreacted bis(2-bromoethyl)ether. The precipitated crude product was purified by column chromatography on SiO2 with CHCl3-MeOH (100:120:1 v/v) as the eluent to provide 2c.

The synthetic route of 5414-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Matsumoto, Jin; Kubo, Tomoya; Shinbara, Tomohiko; Matsuda, Naomi; Shiragami, Tsutomu; Fujitsuka, Mamoru; Majima, Tetsuro; Yasuda, Masahide; Bulletin of the Chemical Society of Japan; vol. 86; 11; (2013); p. 1240 – 1247;,
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Related Products of 873980-68-8,Some common heterocyclic compound, 873980-68-8, name is 4-Bromo-2-methoxy-5-methylaniline, molecular formula is C8H10BrNO, 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 solution of 4-bromo-2-methoxy-5-methylaniline (4.0 g, 18 mmol) in MeOH (200 mL) was added KSCN (3.6 g, 37 mmol) and CUSO4 (14.9 g, 93 mmol). The reaction mixture was stirred at 80C overnight. The reaction mixture was quenched with aq. NH3 (7M, 200 mL), extracted with EtOAc (3 chi 200 mL) and washed with brine (200 mL). It was dried over Na2S04, filtered and concentrated. The residue was purified by silica gel chromatography (0%) to 10%) MeOH in DCM) to give 6-bromo-4-methoxy-7-methylbenzo[d]thiazol-2-amine (2.0 g, 39.5%) as a yellow solid. MS (ES+) C9H9BrN20S, requires: 272, found: 274 [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 4-Bromo-2-methoxy-5-methylaniline, its application will become more common.

Reference:
Patent; TESARO, INC.; JONES, Philip; CZAKO, Barbara; BURKE, Jason P.; CROSS, Jason; LEONARD, Paul Graham; TREMBLAY, Martin; MANDAL, Pijus; (232 pag.)WO2018/119387; (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. 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C18H21NO4

General procedure: DCC (0.47 mmol, 1.2 eq.); the N-Fmoc-protected amino acid (0.472 mmol, 1.2 eq) and HOBt·H2O (0.47 mmol, 1.2 eq) were added to a solution of the 30-aminocombretastatin (0.39 mmol, 1 eq) in anhydrous DMF (1.3 mL). The reaction mixture was stirred under N2 atmosphere for 16 h. Then, it was ltered, and the ltrate was poured into a saturated aqueous NH4Cl solution and then extracted with AcOEt (3×15 mL). The combined organic extracts were washed 2 times with water and brine and dried over anhydrous MgSO4. After ltration and evaporation of the solvent under reduced pressure, the resulting residue was chromatographed on silica gel with Hexanes-AcOEt (6:4) to aord the corresponding N-Fmoc-protected derivatives 7 and 9.

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 162705-07-9.

Reference:
Article; Agut, Rauel; Alberto Marco, J.; Carda, Miguel; Falomir, Eva; Gil-Edo, Raquel; Martin-Beltran, Celia; Murga, Juan; Pla, Alberto; Molecules; vol. 25; 3; (2020);,
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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. 107622-80-0, name is (4-Phenoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Computed Properties of C13H13NO

Example 71 3-Hydroxy-4-methoxy-N-(4′-phenoxybenzyl)picolinamide: The procedure of Example 39 was repeated, except that 4-benzyloxyaniline hydrochloride was changed to 4-phenoxybenzylamine. Thus, the title compound was prepared.

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; Meiji Seika Kaisha, Ltd.; EP1134214; (2001); A1;,
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74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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. name: 1,3-Dibromo-5-methoxybenzene

General procedure: Typically, TDPP (200 mg, 0.27 mmol), dibromobenzene derivatives 0.11 mmol, anhydrous Cs2CO3(200 mg, 0.61 mmol), PivOH (7.9 mg, 0.08 mmol), Pd2(dba)3 (4.00 mg, 1.5 mol%), tris(o-methoxyphenyl)phosphine (3.08 mg, 3 mol%) were successively added into a Schlenk tube. The tube was purged by three repetitions of vacuum and argon filling. Then, 5 mL anhydrous toluene was added via syringe.The reaction solution was deoxygenated using three freeze-vacuum-thaw cycles, and then rigorouslystirred at 100 C for 24 h under argon atmosphere. Removal of the toluene by rotary evaporatoraorded the crude product, which was then purified by chromatogragh column (CC) on silica gelusing a mixture of CH2Cl2 and hexane as eluent, giving the target molecules Ms1~9.

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

Reference:
Article; Liu, Hui; Zhang, Xiao-Feng; Cheng, Jing-Zhao; Zhong, Ai-Guo; Wen, He-Rui; Liu, Shi-Yong; Molecules; vol. 24; 9; (2019);,
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