Month: August 2021

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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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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Electric Literature of 20781-20-8, A common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, molecular formula is C9H13NO2, 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: The 6-chloronicotinic acid (2g, 12.73 mmol) was dissolved inDMF (20 ml). In the prepared solution, TBTU (4.90 g, 15.28 mmol)and TEA (2.66 mL, 19.10 mmol) was added. The reaction mixture was stirred for 30 min at room temperature. An amine(12.73 mmol) was added and stirred for 3 h at room temperature.The progress of the reaction was monitored by TLC. The reactionmixture was then quenched with crushed ice (50g) and stirred for30 min. The obtained precipitate was filtered and dried. Finally the product was purified by column chromatography using ethyl acetate:petroleum ether as eluent. Yield: (2a:87%, 2c:86%, 2l: 88%).

The synthetic route of 20781-20-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Thirunavukarasu, Jayaprakash; Begam, Rosina; Shajahan; Journal of Molecular Structure; vol. 1196; (2019); p. 518 – 526;,
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Synthetic Route of 126829-31-0,Some common heterocyclic compound, 126829-31-0, name is 2-Ethynyl-1,3-dimethoxybenzene, molecular formula is C10H10O2, 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 THF solution (0.2 mL) of PdCl2(MeCN)2 (3.9 mg, 0.015 mmol) and 2b (10.2 mg, 0.015 mmol) was stirred for 10 min. To the solution were added diiodoparacyclophane 6 (0.05 mmol) in THF (0.8 mL), i-Pr2NH (0.2mL), alkyne 7 (0.2 mmol) and CuI (2.9 mg, 0.015 mmol) in order. The resulting mixture was stirred at room temperature. After the reaction was complete, H2O was added to the reaction mixture, and organic materials were extracted with AcOEt. The organic layer was washed with brine and dried with Na2SO4. The solvent was removed under reduced pressure, and the crude products were purified by thin-layer chromatography to give dialkynylated product 8.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Ethynyl-1,3-dimethoxybenzene, its application will become more common.

Reference:
Article; Kanda, Kazumasa; Oshima, Shoya; Shizuno, Tsubasa; Hamanaka, Risa; Fukai, Miku; Shibata, Takanori; Heterocycles; vol. 8; 2; (2014); p. 1355 – 1370;,
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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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Reference of 2050-46-6, 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. 2050-46-6, name is 1,2-Diethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 7 Synthesis of 1,2-Diethoxy-4-(5′-hexynoyl)benzene STR23 A solution of 1,2-diethoxybenzene (1.66 g, 10.0 mmol) and 5-hexynoyl chloride (1.31 g, 1.00 eq) in methylene chloride (20 ml) is cooled to -60 C. Stannic chloride (2.66 g, 1.02 eq) is slowly added to the solution and the mixture is stirred at -60 C. for 10 minutes. The reaction mixture is quenched with 3N HCl and the layers are separated. The methylene chloride layer is extracted with 3N HCl, then extracted twice with water, and concentrated in vacuo. The yield of the crude 1,2-diethoxy-4-(5′-hexynoyl)benzene is 2.67 g.

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

Reference:
Patent; Norwich Eaton Pharmaceuticals, Inc.; US4982006; (1991); A;,
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Some common heterocyclic compound, 801282-00-8, name is 2-Fluoro-3-methoxyaniline, molecular formula is C7H8FNO, 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: 2-Fluoro-3-methoxyaniline

Aniline D3 (1.18 g, 8.36 MMOL) was combined with dimethylacetylene dicarboxylate A3 (1.45 mL, 10.0 MMOL) in methanol (25 mL). The reaction was REFLUXED for 2 hours before being concentrated to dryness. The crude material was purified by flash chromatography eluting with 9/1 (hexane/EtOAc) to give the Michael adduct D4 as a yellow oil, (1. 27 g, 54%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 801282-00-8, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO KG; WO2004/103996; (2004); A1;,
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These common heterocyclic compound, 1978-39-8, name is 5-Fluoro-2-methoxyaniline, 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: 5-Fluoro-2-methoxyaniline

Step (b): Preparation of 1-(4-fluoro-2-methoxyphenyl)piperazine Reaction of bis(2-chloroethyl)amine hydrochloride (0.11 mol) with 5-fluoro-2-methoxyaniline (0.01 mol) according to Step (c) of Example XII, provided 19.5 g (95% yield) of the piperazine intermediate used without further purification.

The synthetic route of 5-Fluoro-2-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Company; US4585773; (1986); A;,
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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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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. 111-95-5, name is Bis(2-methoxyethyl)amine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 111-95-5

mixture of 4 3,6-diaminopyrazine-2,5-dicarboxylic acid (200 mg, 1.01 mmol), 5 bis-2-(methoxyethyl)amine (372 muL, 335.5 mg, 2.52 mmol), HOBt.H2O (459 mg, 3.00 mmol), and 6 EDC.HCl (575 mg, 3.00 mmol) were stirred together in 7 DMF (20 mL) for 1 h at room temperature. The mixture was concentrated to dryness and the residue was partitioned with EtOAc and water. The layers were separated and the 8 EtOAc solution was washed with saturated NaHCO3 and brine. The solution was dried over anhydrous Na2SO4, filtered and concentrated. Purification by radial flash chromatography (SiO2, 10/1 CHCl3-MeOH) afforded 228.7 mg (53% yield) of Example 1 as an orange foam: 1H NMR (300 MHz, CDCl3), delta 4.92 (s, 4H), 3.76 (apparent t, J=5.4 Hz, 4H), 3.70 (apparent t, J=5.6 Hz, 4H), 3.64 (apparent t, J=5.4 Hz, 4H), 3.565 (apparent t, J=5.4 Hz), 3.67 (s, 6H), 3.28 (s, 6H). 13C NMR (75 MHz, CDCl3) delta 167.6 (s), 145.6 (s), 131.0 (s), 72.0 (t), 70.8 (t), 59.2 (q), 49.7 (t), 47.1 (t). LCMS (5-95% gradient acetonitrile in 0.1% TFA over 10 min), single peak retention time=3.14 min on 30 mm column, (M+H)+=429. UV/vis (100 muM in PBS) lambdaabs=394 nm. Fluorescence (100 nm) lambdaex=394 nm lambdaem=550 nm.

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 111-95-5.

Reference:
Patent; MediBeacon Inc.; Debreczeny, Martin P.; Rajagopalan, Raghavan; Dorshow, Richard B.; Neumann, William L.; Rogers, Thomas E.; (54 pag.)US2019/125901; (2019); A1;,
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