Heterocyclic Building Blocks-quinoxaline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6639-87-8,6-Nitroquinoxaline,as a common compound, the synthetic route is as follows.

6639-87-8, [0170] To a solution of 6-nitroquinoxaline (2.2 g, 12.57 mmol, 1.0 eq) in MeOH, was added dropwise Ranney-Ni (0.7 mL) and hydrazine hydrate (5 mL) was added at 0 C. The mixture was stirred for 2 h at RT. The mixture was filtered and washed with MeOH. The solid was dried under vacuo to give the product (1.8 g, yield: 98.75%>). LC/MS: m/z (M++l) = 146. 42C. Preparation of N-methylquinoxalin-6-amine

As the paragraph descriping shows that 6639-87-8 is playing an increasingly important role.

Reference£º
Patent; PHARMARESOURCES (SHANGHAI) CO., LTD.; CHEN, Ping; ZHOU, Ding; SHAO, Shaoping; CAI, Zhen-wei; WO2013/6792; (2013); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.32601-86-8,2-Chloro-3-methylquinoxaline,as a common compound, the synthetic route is as follows.

INTERMEDIATE: (3-Methyl-quinoxalin-2-yl)-hydrazine (Ha). 2-Oxo-propanoic acid methyl ester (9.0 mL) was added to a solution of 1,2-benzenediamine (10.8 g) in methanol (80 mL). The resulting suspension was refluxed for 10 min before it was cooled to ambient temperature. The precipitated solid was filtered off and dried to afford 3-methyl-lH-quinoxalin-2-one (15.3 g) sufficiently pure for the next step. 1.60 g of this material was dissolved in phosphoryl chloride (10 mL) and heated under MW conditions at 130 C for 0.5h. The volatiles were removed in vacuo, and the residue was treated with ice/water to quench excess phosphoryl chloride. Diethyl ether and brine were added and the organic layer was dried over Na2SO i, filtered, and concentrated in vacuo to afford 2-chloro-3- methyl-quinoxaline (1.7 g) sufficiently pure for the next step. This material was dissolved in ethanol (150 mL) and hydrazine hydrate (2.43 mL) was added. The mixture was refluxed for 1.5h. The volatiles were removed in vacuo, and the residual solid was washed with water, filtered off and dried Ila (1.2 g) sufficiently pure for the next step., 32601-86-8

32601-86-8 2-Chloro-3-methylquinoxaline 236276, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; H. LUNDBECK A/S; J?RGENSEN, Morten; BRUUN, Anne, Techau; RASMUSSEN, Lars, Kyhn; LARSEN, Mogens; WO2013/34755; (2013); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.80636-30-2,3,3-Dimethyl-3,4-dihydroquinoxalin-2(1H)-one,as a common compound, the synthetic route is as follows.

80636-30-2, A solution of the compound obtained in the above step (1) (300 mg) in concentrated sulfuric acid (12 mL) was cooled to -15 C, and thereto was added dropwise a solution of nitric acid (44 muL) in concentrated sulfuric acid (0.6 mL). The mixture was stirred at the same temperature for 3 hours. To the reaction mixture was added sodium hydroxide (5.4 g) and ice, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was suspended in ethyl acetate- diethylether, and the precipitates were collected by filtration. The resultant solid was purified by column chromatography on NH-silica gel (Chromatorex NH-silica gel, solvent; n-hexane/ethyl acetate = 4/1 ? 1/4) to give 3,3-dimethyl-6-nitro-3,4- dihydro- quinoxalin-2(lH)-one (26 mg) as a yellow powder. MS(APCI) m/z: 222 [M+H]+

As the paragraph descriping shows that 80636-30-2 is playing an increasingly important role.

Reference£º
Patent; TANABE SEIYAKU CO., LTD.; WO2007/89034; (2007); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.212327-10-1,7-Bromo-2-methoxyquinoxaline,as a common compound, the synthetic route is as follows.

Under an argon atmosphere, 140 mg (0.586 mmol) of example 74A was dissolved in 15 ml dioxane. Then 172 mg (1.76 mmol) potassium acetate, 38 mg (0.047 mmol) of 1,1 ‘-bis- (diphenylphosphino)ferrocene palladium(II) chloride-dichloromethane complex and 163 mg (0.644 mmol) of 4,4,4’4l5,5,5’5′-octamethyl-2,2’-bi-l,3,2-dioxaborolan were added. The reaction mixture was stirred overnight at 1300C oil bath temperature. After cooling, dioxane was added to the reaction mixture and it was filtered on kieselguhr. It was washed again with ethyl acetate. The filtrate was concentrated in a rotary evaporator at reduced pressure and dried under high vacuum. We obtained 152 mg of 2-methoxy-7-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)quinoxaline as raw product. This was reacted subsequently without further purification., 212327-10-1

As the paragraph descriping shows that 212327-10-1 is playing an increasingly important role.

Reference£º
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; KAST, Raimund; GRIEBENOW, Nils; MEIER, Heinrich; KOLKHOF, Peter; ALBRECHT-KUePPER, Barbara; NITSCHE, Adam; STASCH, Johannes-Peter; SCHNEIDER, Dirk; TEUSCH, Nicole; RUDOLPH, Joachim; WHELAN, James; BULLOCK, William; PLEASIC-WILLIAMS, Susan; WO2010/20363; (2010); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6925-00-4,Quinoxaline-6-carboxylic acid,as a common compound, the synthetic route is as follows.

A mixture of quinoline-6-carboxylic acid (3.48 g; 20 mmol) and thionylchloride (10 ml; 137 mmol) was stirred at 60 C. for 4 hours. The mixture was allowed to cool to room temperature. The solid quinoline-6-carboxylic acid chloride was washed with diethyl ether., 6925-00-4

6925-00-4 Quinoxaline-6-carboxylic acid 674813, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; Peters, Dan; Christensen, Jeppe Kejser; Harps¡ãe, Kasper; Liljefors, Tommy; US2009/286797; (2009); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1593-08-4,2-Formylquinoxaline,as a common compound, the synthetic route is as follows.

General procedure: The aniline (10 mmol) was combined with the aldehyde (10 mmol) in 20 mL of absolute ethanol. To this solution was added glacial acetic acid (ca. 0.1 mL) and the mixture is stirred at room temperature for 12 h. The solvent was then removed and the crude product was dried under high vacuum for overnight to give pure imine product with quantitative yield.

1593-08-4, The synthetic route of 1593-08-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Vuong, Hien; Klumpp, Douglas A.; Synthetic Communications; vol. 49; 2; (2019); p. 316 – 323;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6344-72-5,6-Methylquinoxaline,as a common compound, the synthetic route is as follows.

6344-72-5, Example 10 Synthesis of 6-n-butylaminomethyl-quinoxaline In a 50 ml flask, 6-methyl-quinoxaline (1.25 g, 8.68 mmol) was dissolved together with N-bromosuccinimide (2.32 g, 13.0 mmol) and benzoyl-peroxide (0.15 g, 0.62 mmol) in 31 g of chlorobenzene. The solution was stirred with heating at 85 C for 2.0 hours to yield a reddish solution. The solution was cooled down to room temperature and one volume of pentane was added to facilitate the removal of succinimides. The precipitate was washed with pentane and the extracts were combined with the chlorobenzene solution. The yellow solution was vacuum dried to give a yellow residue mainly composed of 6-bromomethyl-quinoxaline. The yellow solid was dissolved in 19.0 g of n-butylamine to give a yellow solution that was stirred at room temperature for ~5 minutes. Analysis of a sample showed that the 6-bromomethyl-quinoxaline was consumed to give exclusively 6-n-butylaminomethyl-quinoxaline as a deep yellow oil (1.71 g, 92% over all yield). MS (70 ev): 215 M+, 172 (M+-CH3-CH2-CH2), 143 (M+-CH3-CH2-CH2-CH2).

6344-72-5 6-Methylquinoxaline 242567, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; Air Products and Chemicals, Inc.; US6548670; (2003); B1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.887590-25-2,tert-Butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of tert-butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate obtained in Reference Example 28 (1.06 g) in tetrahydrofuran (20 ml), sodium hydride (60% suspension in oil, 181 mg) was added and stirred for 5 minutes, followed by addition of methyl iodide (281 mul). After stirring at room temperature for 1 hour, sodium hydride (60% suspension in oil, 181 mg) was further added and stirred for 30 minutes, followed by addition of methyl iodide (281 mul). After stirring overnight at room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed sequentially with water and brine, and then dried over anhydrous sodium sulfate. After the desiccant was filtered off, the solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate = 10:1 to 5:1) to give tert-butyl 4-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate (331 mg) as a brown powder. To a solution of tert-butyl 4-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate thus obtained (331 mg) in ethyl acetate (2 ml), 4N hydrochloric acid (in ethyl acetate, 1.1 ml) was added and stirred overnight at room temperature. The reaction mixture was diluted with 8M aqueous sodium hydroxide and then extracted with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. After the desiccant was filtered off, the solvent was distilled off under reduced pressure to give the titled compound, i.e., 1-methyl-1,2,3,4-tetrahydroquinoxaline (179 mg) as a brown oil. 1H NMR (300 MHz, CHLOROFORM-D) delta 2.86 (s, 3 H), 3.23-3.31 (m, 2 H), 3.44-3.52 (m, 2 H), 3.68 (brs, 1 H), 6.43-6.51 (m, 1 H), 6.53-6.62 (m, 2 H), 6.63-6.72 (m, 1 H)., 887590-25-2

The synthetic route of 887590-25-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Taisho Pharmaceutical Co. Ltd.; EP2172453; (2010); A1;,
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67074-63-9, 4-Methyl-3,4-dihydroquinoxalin-2(1H)-one is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

24c. 1,2,3,4-tetrahydroquinoxaline To a solution of 24b (300 mg, 1.85 mmol) in THF (2 mL) was added 1N LiAlH4 (10 mL, 10 mmol). The reaction mixture was stirred at rt for 1 h. The reaction mixture was quenched with H2O (1 mL) at 0 C., 15% NaOH (1 mL), followed by H2O (1 mL). The reaction mixture was extracted with EtOAc. The EtOAc was then washed with brine, dried over Na2SO4. The solvent was evaporated under reduced pressure to afford 24c (260 mg, 95%) as white powder. LC-MS ESI m/z 149 [M+H]+., 67074-63-9

As the paragraph descriping shows that 67074-63-9 is playing an increasingly important role.

Reference£º
Patent; Tuerdi, Huji; Chao, Hannguang J.; Qiao, Jennifer X.; Wang, Tammy C.; Gungor, Timur; US2005/261244; (2005); A1;,
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50998-17-9, 6-Bromoquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A mixture of methyl 4-bromobenzoate2a (100 mg, 0.465 mmol), methyl N-(tert-butoxycarbonyl)glycinate 3a (132 mg, 0.698 mmol), Pd2(dba)3 (8.5 mg,9.3 lmol), Xantphos (16 mg, 0.028 mmol), and cesium carbonate(303 mg, 0.930 mmol) was charged with dioxane (1.0 mL). Theresulting suspension was sparged with argon via subsurface bubblingfor 5 min, and the reaction mixture was sealed and stirredat 100 C for 12 h. The reaction was cooled to ambient temperature,diluted with EtOAc (20 mL), and filtered to remove the inorganicsalts. The filtrate was concentrated to an oil, then purified bycolumn chromatography on silica gel, eluting with an EtOAc/hexanesgradient (2-30%) to afford the desired product 4a as a colorlessgum (75% isolated yield). 1H NMR (500 MHz, DMSO-d6): d 7.90(d, J = 9.0 Hz, 2H), 7.40 (d, J = 8.5 Hz, 2H), 4.39 (s, 2H), 3.83 (s, 3H),3.68 (s, 3H), 1.37 (s, 9H). LRMS (ESI) calcd for C16H21NO6 (M+Na)+:346.1, found: 346.1., 50998-17-9

The synthetic route of 50998-17-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Falcone, Danielle; Osimboni, Ekundayo; Guerin, David J.; Tetrahedron Letters; vol. 55; 16; (2014); p. 2646 – 2648;,
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