Tag: M.W=200-300

Reference of 36805-97-7, A common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, 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.

To a solution of compound 36 (5.67 mmol) in anhydrous toluene (13 mL) at 110 0C was added Lambdaf,Lambda/-dimethylformamide di- tert-butylacetal (22.7 mmol) dropwise. The reaction mixture was refluxed for 1.5 hrs. The mixture was cooled down to room temperature, and washed sequentially with H2O (30 mL), sat NaHCO3 (30 ml), and brine (30 ml). Organics were dried and concentrated under reduced pressure to yield compound 37 as a yellow oil in 82% yield.

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; IDENIX PHARMACEUTICALS, INC.; PARSY, Christophe Claude; ALEXANDRE, Francois-Rene; LEROY, Frederic; CONVARD, Thierry; SURLERAUX, Dominique; WO2011/17389; (2011); A1;,
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63057-72-7, name is 1-(Benzyloxy)-4-bromo-2-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-(Benzyloxy)-4-bromo-2-methoxybenzene

General procedure: n-BuLi (10.7 mmol, 1.6 M solution in hexanes) was slowly added at -78 C under N2 atm to a stirred solution of 1a (10.2 mmol) in THF (25 mL) then stirred for 30 min at the same temperature. Aldehyde 2a (11.3 mmol) in THF (25 mL) was added dropwise over a period of 5 min then the reaction mixture was stirred for 30 min at -78 C. The reaction mixture was allowed to warm to 0 C, quenched with saturated NH4Cl solution, and extracted into ethyl acetate. The organic layer was dried over anhydrous Na2SO4, and the solvents were evaporated. The crude compound was purified by column chromatography (35% EtOAc/hexane) to get alcohol 3a as off-white solid (yield 55%).

The synthetic route of 63057-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pericherla, Kasiviswanadharaju; Shirazi, Amir Nasrolahi; Kameshwara Rao; Tiwari, Rakesh K.; Dasilva, Nicholas; McCaffrey, Kellen T.; Beni, Yousef A.; Gonzalez-Sarrias, Antonio; Seeram, Navindra P.; Parang, Keykavous; Kumar, Anil; Bioorganic and Medicinal Chemistry Letters; vol. 23; 19; (2013); p. 5329 – 5331;,
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24988-36-1, name is 1,5-Dibromo-2,4-dimethoxybenzene, 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

4,6-Dimethoxy-1,3-dibromobenzene21 (1.50 g, 5.07 mmol) was added to a solution of i-PrMgCl (1 M in THF, 7 mL, 7 mmol) at -10 C under N2 atmosphere. After 45 min, methyl iodide (0.5 mL, 7.7 mmol) was added drop wise, and the mixture was allowed to stir at the same temperature for 30 min and then at rt for 4 h. The reaction was quenched by the addition of 10% HCl (15 mL). THF was removed in vacuum, and the mixture was extracted with ethyl acetate (2*50 mL). The organic layer was washed with water (2*30 mL) and brine (20 mL), dried (Na2SO4), filtered, and concentrated. The resulting crude compound was purified by column chromatography to get 8 (950 mg, 81%) as a colorless liquid. Rf 0.6 (1:10 ethyl acetate:hexane); numax (film) cm-1 1555, 1222, 1143, 1045; 1H NMR (CDCl3, 500 MHz): delta 7.24 (s, 1H, C6-H), 6.42 (s, 1H, C3-H), 3.87 (s, 3H, OCH3), 3.81 (s, 3H, OCH3), 2.1 (s, 3H, CH3); 13C NMR (CDCl3,125 MHz): delta 157.8 (C), 154.6 (C), 133.8 (CH), 120.0 (C), 100.8 (C), 96.2 (CH), 56.3 (CH3), 55.5 (CH3), 15.1 (CH3); HRMS (EI+) m/z 229.9946 ([M]+ C9H11BrO2, requires 229.9942).

The synthetic route of 24988-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pahari, Pallab; Saikia, Ujwal Pratim; Das, Trinath Prasad; Damodaran, Chendil; Rohr, Juergen; Tetrahedron; vol. 72; 23; (2016); p. 3324 – 3334;,
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Related Products of 13070-45-6, A common heterocyclic compound, 13070-45-6, name is 6-Methoxy-1,2,3,4-tetrahydrocarbazole, molecular formula is C13H15NO, 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.

General procedure: A stirred solution of acrylate 9 (1 mmol), cycloalkaneindole 10a,b, 11a-j, 12a,b, or 13a,b, (1 mmol), CsF (0.1 g), and hydroquinone (0.02 g) in DMF (1.5 mL) was heated at 120-140C for 4 h. The solvent was removed in vacuo (3 Torr), the residue was extracted with dichloromethane, the solvent was removed in vacuo. Column chromatography of the residue (silica gel (60 mesh), elution with methanol-chloroform, 1 : 10) afforded target compounds. This procedure was applied for the synthesis of the following compounds: 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(2,3dihydro-1H-cyclopenta[b]indol-4-yl)propan-1-one hydrochloride (14a), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(7-methyl-2,3-dihydro-1H-cyclopenta[b]indol-4-yl)propan-1-one (14b), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15a), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-methyl-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15b), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-fluoro-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15c), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-methoxy-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15d), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-trifluoromethoxy-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15e), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(3-methyl-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15f), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(3,6-dimethyl-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15g), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-fluoro-3-methyl-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15h), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(3-methyl-6-methoxy-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15i), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(3methyl-6-trifluoromethoxy-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15j), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(7,8,9,10-tetrahydro-6H-cyclohepta[b]indol-4-yl)propan-1-one (16a), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(2-methyl-7,8,9,10-tetrahydro-6H-cyclohepta[b]indol-4-yl)propan-1-one (16b), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6,7,8,9,10,11-hexahydrocycloocta[b]indol-5-yl)propan-1-one (17a), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(2-methyl-6,7,8,9,10,11-hexahydrocycloocta[b]indol-5-yl)propan-1-one (17b).

The synthetic route of 13070-45-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bachurin; Sokolov; Aksinenko; Epishina; Goreva; Gabre?yan; Grigo?ev; Russian Chemical Bulletin; vol. 64; 6; (2015); p. 1354 – 1361; Izv. Akad. Nauk, Ser. Khim.; 6; (2015); p. 1354 – 1361,7;,
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Application of 36805-97-7, These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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.

To a solution of 1-pyrazol [1,5-b] [PYRIDAZIN-3-YLETHANONE] (8.5 g, 52.7 [MMOL)] in DMF (100 mL) was added [DIMETHYLFORMAMIDE] di-tert-butylacetal (16.1 g, 79.2 [MMOL).] The reaction was heated at an oil bath temperature of 100 [C] for about 4 hours. The solvent was removed in vacuo. The residue was triturated with diethyl ether to give the title compound as a brown solid (8 g, 70%). 1H-NMR (300 MHz, [D6-DMSO) 6] 8.76 (dd, 1H, J = 10.0, 2. [0 HZ),] 8.74 (s, [1H),] 8.61 (dd, [1 H, J = 4.] 0,2. [0 HZ),] 7.74 (d, 1H, J = 12 Hz), 7.44 (dd, [1H,] J = 10.0, 4.0 Hz), 5.87 (d, [1H,] J = 12 Hz), 3.18 (bs, 3H), 2.97 (bs, 3H); MS [(ESI)] (M+H) [+] 217.

The synthetic route of 36805-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/35588; (2004); A1;,
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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 1462-37-9 as follows. Recommanded Product: ((2-Bromoethoxy)methyl)benzene

To a suspension of NaH (13.0 g, 0.32 mol) in THF (70 mL) was added malonic acid diethyl ester (51.9 g, 0.32 mol) drop wise at 0°C. When no more gas was formed reagent 1 (57.2 g, 0.27 mol) was added. The mixture was stirred at 75°C for 5 h. The mixture was allowed to reach room temperature and then quenched with water (300 mL). The mixture was extracted with MTBE (250 mL x 3). The combined organic layers were dried over MgS04 and evaporated to dryness. Flash chromatography (silica, petroleum ether: EtOAc 20:1 to 10:1 ) gave reagent 2 as a colorless oil (69.6 g, 74percent). 1H NMR (CDCI3) delta 7.24-7.34 (m, 5 H), 4.42 (s, 2 H), 4.10-4.22 (m, 4 H), 3.57 (t, J = 7.2 Hz, 1 H), 3.51 (t, J = 6.4 Hz, 1 H), 3.33 (s, 1 H), 2.17- 2.22 (m, 2 H), 1 .20-1.28 (m, 6 H).

According to the analysis of related databases, 1462-37-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; ESKILDSEN, J°rgen; WO2014/49133; (2014); A1;,
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Electric Literature of 886762-08-9, These common heterocyclic compound, 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, 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.

General procedure: A solution of substituted anilines (12.4 mmol) dissolved in 30 mL anhydrous THF was added very slowly into a stirred solution of triphosgene (1.40 g, 4.80 mmol) in 20 mL of THF. After stirringfor 15 min, triethylamine (2.90 mL, 20.6 mmol) was then added slowly to the reaction mixture. Stirring was continued for 20 min, various aromatic heterocyclic amines (12.0 mmol) in anhydrous THF (20 mL) was added directly to the above residue. After completion of the action, the reaction was quenched with dilute NaHCO3 and the solvent was subsequently removed in vacuo and extracted with ethyl acetate (3 30 mL). The organic layer was washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silicagel flash chromatography (PE/AcOEt = 5:1) gave as white solid (3a-3h) (yield: 30-50%).

Statistics shows that 5-Bromo-2-(trifluoromethoxy)aniline is playing an increasingly important role. we look forward to future research findings about 886762-08-9.

Reference:
Article; Shan, Yuanyuan; Wang, Chen; Zhang, Lin; Wang, Jinfeng; Wang, Maoyi; Dong, Yalin; Bioorganic and Medicinal Chemistry; vol. 24; 4; (2016); p. 750 – 758;,
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Related Products of 25245-34-5, 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. 25245-34-5 name is 2-Bromo-1,4-dimethoxybenzene, 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 1-L round-bottom flask reactor, 2-bromo-1,4-dimethoxybenzene (50 g, 230 mmol) and tetrahydrofuran (400 ml) were dissolved. After the mixture was cooled to -78 C., it was added with drops of N-butyl lithium (167 ml, 280 mmol). At the same temperature, the mixture was stirred for 2 hrs before the addition of trimethyl borate (36 ml, 320 mmol). Stirring was conducted overnight at room temperature. After completion of the reaction, 2 N HCl was dropwise added for acidification. Extraction with water and ethyl acetate gave an organic layer which was then dried over magnesium sulfate and concentrated in a vacuum. Recrystallization in heptane and toluene afforded . (20.8 g, 50%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1,4-dimethoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; SFC CO., LTD.; Cha, Soon-Wook; Park, Young-Hwan; Yoon, Seo-Yeon; Shim, So Young; (152 pag.)US2017/18723; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, 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 29578-39-0, category: ethers-buliding-blocks

To a solution of 9-1 (20 g, 97.55 mmol) in tetrahydrofuran (100 mL) was added dropwise n-butyl lithium (43 mL, 2.5 M, 107.3 mmol) at -78 C. It was stirred for 30 minutes and N,N-dimethylformamide (15.1 mL, 195.1 mmol) was added at this temperature. It was stirred for another 30 minutes and the cold bath was removed. After 1 hour, the reaction was quenched with saturated aqueous ammonium chloride. The organic layer was washed with water and saturated aqueous sodium chloride, dried (sodium sulfate), filtered and concentrated. The residue was purified by chromatography on silica to give 9-2.

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; NEUROVIVE PHARMACEUTICAL AB; Moss, Steven James; Gregory, Matthew Alan; Wilkinson, Barrie; US9139613; (2015); B2;,
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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. 1663-61-2, name is (Triethoxymethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

General procedure: The 2-aminobenzamide (1 equiv), the orthoester (2?3 equiv) and absolute ethanol (2?3 mL) wereplaced in a 15-mL Chemglass screw-cap pressure tube (No. CG-1880-01, Chemglass, Vineland, NJ,USA). Glacial acetic acid (3 equiv) was added, N2 was introduced to the vessel and the cap wastightened. The vessel was heated at 110 °C for 12?72 h, then cooled and concentrated to give thequinazolinone, which was purified by crystallization from absolute ethanol or trituration from 5percentether in pentane. The following compounds were prepared:

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 1663-61-2.

Reference:
Article; Gavin, Joshua T.; Annor-Gyamfi, Joel K.; Bunce, Richard A.; Molecules; vol. 23; 11; (2018);,
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