Day: November 16, 2020

50998-17-9, 6-Bromoquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,50998-17-9

EXAMPLE 622,5-Dimethyl-5-[3-(quinoxalin-6-yl)phenyl1tetrahydrofuran-2-ol6-Bromoquinoxaline (3.14 g, 15 mmol) was dissolved in DME/water (9:1, 500 niL), and 3-acetylphenylboronic acid (2.5 g, 15 mmol), cesium carbonate (9.75 g, 30 mmol) and Pd(PPh3 )4 (870 mg, 0.75 mmol) were added. The mixture was heated to 1100C for 18 h. After cooling, the mixture was partitioned between EtOAc and water (100 mL each), and the organic phase concentrated in vacuo. The residue was triturated with diethyl ether (50 mL) to give l-[3-(quinoxalin-6-yl)phenyl]ethanone (3.8 g, >95%). LCMS (ES+) 249.2 (M+H)+, RT 3.04 minutes. A sample of this material (500 mg, 2 mmol) was dissolved in THF (4 mL), and cooled to O0C. But-l-en-4-ylmagnesium bromide (0.5M in THF, 4 mL, 2 mmol) was added and the mixture allowed to warm to room temperature. After stirring for 2 h, water (2 mL) was added. The organic phase was passed though a silica plug and concentrated in vacuo. The residue was dissolved in DCM (3 mL). 7V-Bromosuccinimide (146 mg, 0.9 mmol) was added and the mixture stirred at room temperature for 18 h. The mixture was partitioned between DCM (5 mL) and saturated sodium hydrogencarbonate solution (5 mL). The organic phase was passed through a silica plug and the filtrate concentrated in vacuo. The residue was dissolved in MeOH (3 mL). Sodium methoxide (200 mg) was added and the mixture was stirred at 600C for 3 days. The mixture was neutralized to pH 7.0 with IM hydrochloric acid and then concentrated in vacuo. The residue was purified by preparative HPLC to isolate the title compound (5 mg, 2:1 mixture of cis:trans isomers). deltaH (CDCl3) 8.89 (d, IH), 8.86 (d, IH), 8.32 (m, IH), 8.20 (m, IH), 8.08 (m, IH), 7.84 (m, IH), 7.62 (m, IH), 7.50 (m, 2H), 2.10-2.58 (m, 4H), 2.11 (s, 3H), 1.56-1.72 (m, 4H). LCMS (ES+) 321.3 (M+H)+, RT 2.93 minutes.

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

Reference£º
Patent; UCB PHARMA S.A.; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MACK, Stephen, Robert; PERRY, Benjamin, Garfield; RAPHY, Gilles; SAVILLE-STONES, Elizabeth, Anne; WO2010/52448; (2010); A2;,
Quinoxaline – Wikipedia
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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.

(3) To a solution of 4-chloro-2-(hydroxymethyl)-6-pyrrolidin-1-ylpyrimidine (1.00 g, 4.68 mmol) and 2-chloro-3-methylquinoxaline (1.25 g, 7.02 mmol) in N,N-dimethylformamide (10 mL) and tetrahydrofuran (20 mL) was added sodium hydride (60% dispersion in mineral oil, 281 mg, 7.02 mmol) at 0 C. The reaction mixture was stirred for 2 hour at room temperature, and then poured into cold water. The mixture was extracted with ethyl acetate and the organic layer was washed with water. The organic layer was dried over magnesium sulfate, filtrated and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3) to give 4-chloro-2-{[(3-methylquinoxalin-2-yl)oxy]methyl}-6-pyrrolidin-1-ylpyrimidine as red powder (1.67 g, quant.). mp 136-140 C. MS (APCI): m/z 356/358 (M+H).

32601-86-8, The synthetic route of 32601-86-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Kawanishi, Eiji; Matsumura, Takehiko; US2011/160206; (2011); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.49679-45-0,Ethyl 3-chloroquinoxaline-2-carboxylate,as a common compound, the synthetic route is as follows.

A suspension of 3-chloroquinoxaline-2-carboxylate (86.0 g, 363 mmol), trimethylboroxine (22.8 g, 0.182 mmol), [1,1 ‘- bis(diphenylphosphino) ferrocene] dichloropalladium(II) (8.90 g, 11.0 mmol), and potassium carbonate (100 g, 727 mmol) in 1,4-dioxane (726 mL) was heated at 115 C for 4 h. And then trimethylboroxine (22.8 g, 0.182 mmol) was added again and heated at same temperature for 2 h. After being cooled to ambient temperature, the reaction mixture was diluted with ethyl acetate (700 mL) and filtrated through celite with ethyl acetate (1000 mL). The filtrate was combined and concentrated in vacuo. The residue was purified by silica gel column chromatography (silica gel 900 g, hexane: ethyl acetate = 9: 1 to 17:3) followed by recrystallization from cold hexane to give ethyl 3- methylquinoxaline-2-carboxylate. MS (APCI): m/z 217 (M+H)., 49679-45-0

49679-45-0 Ethyl 3-chloroquinoxaline-2-carboxylate 12283436, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; MITSUBISHI TANABE PHARMA CORPORATION; KAWANISHI, Eiji; HONGU, Mitsuya; TANAKA, Yoshihito; WO2011/105628; (2011); 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.

Quinoxaline-2-carbaldehyde 626 (1.58 g, 10 mmol) was dissolved in EtOH (150 mL) and 1, 4-xylylenediamine (0.63 g, 4.6 mmol) was then added and mixture was stirred at 75 C for 3 h. The mixture was then cooled to room temp and the precipitate was filtered and washed with EtOH (¡Á3) to give the intermediate diimine as an off-white solid (1.82 g, 95%); mp = 185-186 C. The diimine (1.81 g, 4.3 mmol) was dissolved in MeOH (50 mL) and then cooled over an ice bath. Sodium cyanoborohydride (273 mg, 4.3 mmol) and acetic acid (4 mL) were added to the cooled solution and the suspended solid dissolved gradually whilst the mixture was stirred at room temp for 3 h. The volatile components were evaporated under diminished pressure. Ethyl acetate was then added to residue and this was then washed with aq NaHCO3. The aq layer was further extracted with EtOAc (3 ¡Á 10 mL). The combined organic layer was dried (MgSO4), filtered and the solvent was removed. Chromatography of the residue (EtOAc-MeOH, 2:1) gave 7 as a dark red solid (1.31 g, 72%); mp = 116-117 C; 1H NMR (CDCl3, 500 MHz): delta = 8.88 (s, 2H), 8.05-8.09 (m, 4H), 7.70-7.76 (m, 4H), 7.35 (s, 4H), 4.16 (s, 4H), 3.92 (s, 4H), 2.23 (s, 2H, NH); 13C NMR (125 MHz, CDCl3) delta 154.9 (C), 145.3, 141.9, 141.8 (each CH), 138.7 (C), 130.0, 129.3, 129.2, 129.0, 128.4 (each CH), 53.4, 52.8 (each CH2). HRMS (ESI): Found 443.1960 [M+Na]+, C26H24N6Na requires 443.1968.

1593-08-4, 1593-08-4 2-Formylquinoxaline 594088, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Article; Jarikote, Dilip V.; Li, Wei; Jiang, Tao; Eriksson, Leif A.; Murphy, Paul V.; Bioorganic and Medicinal Chemistry; vol. 19; 2; (2011); p. 826 – 835;,
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879-65-2,879-65-2, 2-Quinoxalinecarboxylic acid is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 67QUINOXALINE-2-CARBOXYLIC ACID [(R)-1-(2-FLUORO-4-METHANESULFONYLAMINO-5-METHYLPHENYL)ETHYL]AMIDE To a stirred solution of quinoxaline-2-carboxylic acid (26 mg, 0.15 mmol), N-[4-((R)-1-aminoethyl)-5-fluoro-2-methylphenyl]methanesulfonamide hydrochloride (35 mg, 0.12 mmol), and N,N,N’,N’-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (56 mg, 0.15 mmol) in N,N-dimethylformamide (0.5 mL) was added N,N-diisopropylethylamine (80 mg, 0.6 mmol). A catalytic amount of DMAP was added, and the reaction was stirred at room temperature for 16 hours. The reaction mixture was concentrated down to a solid. The crude product was suspended in MeOH and filtered, and the filtrate purified by HPLC to give the title compound (25.0 mg, 49%) as an off-white solid. m/z=403.1 (M+1), r.t. 2.83 min. 1H NMR (400 MHz; d6-DMSO) delta 9.43 (1H, s), 9.39 (1H, d), 8.30-8.26 (1H, m), 8.22-8.18 (1H, m), 8.03-7.97 (2H, m), 7.45 (1H, d), 7.11 (1H, d), 5.49-5.39 (1H, m), 3.02 (3H, s), 2.24 (3H, s), 1.57 (3H, d).

As the paragraph descriping shows that 879-65-2 is playing an increasingly important role.

Reference£º
Patent; PFIZER INC.; RENOVIS, INC.; US2012/88746; (2012); A1;,
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887590-25-2, tert-Butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

887590-25-2, 11.2: trans-4-(5-Hydroxyadamantan-2-ylcarbamoyl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester 0.4 g of 3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester is placed in 8 ml of dichloromethane at 0 C. under nitrogen. 0.69 ml of triethylamine and 0.202 g of triphosgene are added. The mixture is stirred at ambient temperature for 3 h, then 1 ml of dimethylformamide and 0.285 g of trans 4-aminoadamantan-1-ol are added and stirring is maintained for 18 h. The reaction medium is washed with a saturated aqueous sodium hydrogencarbonate solution. The organic phase is dried over magnesium sulphate and concentrated to dryness. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of a dichloromethane/methanol (99/1 to 95/5) mixture. 0.54 g of trans-4-(5-hydroxyadamantan-2-ylcarbamoyl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester is obtained. M+H+=428

As the paragraph descriping shows that 887590-25-2 is playing an increasingly important role.

Reference£º
Patent; SANOFI-AVENTIS; US2011/9391; (2011); A1;,
Quinoxaline – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.50998-17-9,6-Bromoquinoxaline,as a common compound, the synthetic route is as follows.,50998-17-9

To a solution of 11e (70.0 mg, 296 mumol), 6-bromoquinoxaline (94.1 mg, 450 mumol), Bu4NOAc (181 mg, 600 mol) and Pd(OAc)2 (10.1 mg, 45.0 mol) in NMP (0.6 mL). The reaction mixture was stirred for 23 h at 100 oC and cooled to room temperature. The mixture was concentrated under reduced pressure. Diluted with water and extracted with EtOAc (3 ¡Á 5 mL). The EtOAc solution was washed with brine (5 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (1:1 hexane/EtOAc) to afford the compound 12d (15 mg, 14%) as a yellow solid. TLC: Rf 0.2 (1:1 hexane/EtOAc). mp: 208-210 oC. 1H-NMR (400 MHz, CDCl3) delta 8.89 (d, 1H, J = 1.6Hz), 8.85 (d, 1H, J = 1.6 Hz), 8.12 (d, 1H, J = 8.4 Hz), 8.07 (d, 1H, J = 1.6 Hz), 7.76 (dd, 1H, J = 8.4 Hz, J = 2.0 Hz), 7.73 (t, 1H, J = 7.6 Hz), 7.64 (d, 1H, J = 7.6 Hz), 7.59-7.57 (m, 2H), 7.30-7.27 (m, 3H), 7.12 (d, 1H, J = 7.6 Hz), 2.18 (s, 3H). 13C-NMR (100 MHz, CDCl3) delta 158.3, 149.1, 146.2, 145.9, 145.8, 143.0, 142.7, 139.1, 132.6, 132.4, 131.6, 131.0, 130.4, 129.5, 128.8, 128.4, 127.8, 123.7, 115.7, 23.8. HRMS (ESI) calcd. for C22H17N6 (M+H): 365.1509; found 365.1512.

50998-17-9 6-Bromoquinoxaline 610939, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Article; Li, Fei; Park, Yunjeong; Hah, Jung-Mi; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry Letters; vol. 23; 4; (2013); p. 1083 – 1086;,
Quinoxaline – Wikipedia
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7467-91-6, Quinoxalin-6-ol is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Underargon, to a solution of 6-ethoxyquinoxaline2(0.29 g, 1.65 mmol) in toluene (20 mL) was added aluminium chloride (0.80 g,5.96 mmol), and the reaction mixture was stirred at 100¡ãC. After 17 h, thereaction mixture was cooled to room temperature, and diluted with 1M aqueousNaOH solution (15 mL) and water (20 mL). The solution was extracted with ethylacetate (60 mL) twice, and the combined organic extracts were washed withbrine, dried over anhydrous Na2SO4, filteredand evaporated under reduced pressure to afford the crude product of 6-hydroxyquinoxalineas a brown oil. This crude product was dissolved in acetone (8.2 mL), and tothe solution were added potassium carbonate (1.14 g, 8.24 mmol) and tert-butylbromoacetate (0.24 mL, 1.64 mmol) at room temperature. The reaction mixture wasstirred at 55¡ãC. After 9 h, the reaction mixture was filtered and washed withacetone. The filtrate was evaporated under reduced pressure, diluted withchloroform, washed with water and brine, dried over anhydrous Na2SO4,filtered and evaporated under reduced pressure. The crude product was purifiedby column chromatography (kanto60N, hexane / ethyl acetate, 5 / 1 to 3 / 1)to afford the tert-butyl ester of the titlecompound as a brown solid (0.22 g, 51percent for 2steps). This ester (0.21 g, 0.83 mmol) was added to 35percent aqueous HCl solution(12 mL), and the reaction mixture was stirred at room temperature. After 7 h,the reaction mixture was evaporated under reduced pressure, and the residue waswashed with diethyl ether to afford the title compound as a brown powder (0.18g, 79percent), 7467-91-6

The synthetic route of 7467-91-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Koda, Hironori; Brazier, John Alan; Onishi, Ippei; Sasaki, Shigeki; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4583 – 4590;,
Quinoxaline – Wikipedia
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6925-00-4,6925-00-4, Quinoxaline-6-carboxylic acid is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of quinoxaline-6-carboxylic acid (2 g, 11.49 mmol) and thionyl chloride (30 mL) was stirred at reflux for 2 hours. The reaction mixture was concentrated to dryness using a rotary evaporator to afford quinoxaline-6- EPO carboxylic acid chloride (crude quantitative). A solution of the above acid chloride (11.49 mmol) in DCM (50 mL) and pyridine (20 mL) was mixed with N,O-dimethyl hydroxylamine HCI salt (2.24 g, 23 mmol) and stirred at room temperature for 12 hours. The reaction was quenched by adding aqueous HCI (50 mL, 1 N), extracted with DCM (3×100 mL), concentrated using a rotary evaporator. The residue was further purified by column (Sitheta2, Hexanes/EtOAc = 1 :3) to yield quinoxaline-6-carboxylic acid methoxy-methyl-amide (2 g, 80%). To a solution of the above Weinreb amide (2.0 g, 9.2 mmol) in THF (30 mL) at O0C was added methyl magnesium bromide (3.9 mL, 11.6 mmol). The reaction mixture was stirred at O0C for 2 hours and then 1 hour at room temperature, quenched by adding aqueous HCI (20 mL, 1 N), extracted with DCM (3×100 mL), concentrated using a rotary evaporator. The residue was further-purified by column (SiO2, Hexanes/EtOAc = 1 :3) to yield 6-acetylquinoxaline (1.17 g, 74%). A solution of 2- chloronicotinic acid ethyl ester (5.0 g, 27 mmol) in MeOH (25 mL) was mixed with sodium methoxide (25.6 mL, 112.5 mmol) and stirred at reflux for 12 hours. The reaction was quenched by adding water (100 mL), extracted with DCM (3×100 mL), concentrated using a rotary evaporator to afford 2-methoxynicotinic acid methyl ester (3.2 g, 71%). A solution of 6-acetylquinoxaline (0.62 g, 3.6 mmol), 2- methoxynicotinic acid methyl ester (0.64 g, 3.8 mmol), and sodium hydride (0.46 g, 11.4 mmol) in THF (100 mL) was stirred at room temperature for 16 hours. The reaction was quenched by adding water (100 mL) and AcOH (20 mL), extracted with dichloromethane (3×100 mL), and concentrated using a rotary evaporator. The residue was re-dissolved in DCM (5 mL) and MeOH (3 mL) and was diluted with Hexanes (50 mL). The solid was removed by filtration and the filtrate was concentrated to afford the diketo compound (0.7 g, 60%). A solution of the above diketone (0.4 g, 1.3 mmol) in AcOH (50 mL) and sulfuric acid (cone, 15 drops) was stirred at reflux for 1 hour. Most of the solvent was removed using a rotary evaporator. The residue was re-dissolved in MeOH and neutralized with potassium carbonate to pH = 8. The solid residue was removed by filtration, washed with MeOH and DCM. The filtrate was extracted with CH2CI2 (3×100 mL) and concentrated using a rotary evaporator. The solid residue was purified by column (SiO2, Hexanes/EtOAc/MeOH = 2:2:1) to afford 2-(quinoxalin-6-yl)-4H- EPO pyrano[2,3-b]pyridin-4-one (90 mg, 24%); MS (ES) m/z: 276 (M+1 ); MP 272.3- 274.80C

As the paragraph descriping shows that 6925-00-4 is playing an increasingly important role.

Reference£º
Patent; RESVERLOGIX CORP.; JOHANSSON, Jan, O.; HANSEN, Henrik, C.; CHIACCHIA, Fabrizio, S.; WONG, Norman, C.W.; WO2007/16525; (2007); A2;,
Quinoxaline – Wikipedia
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76982-23-5, 5-Bromoquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

76982-23-5, 5-Bromoquinoxaline (300 mg, 1.44 mmol) and di-tert-butyl hydrazine-1,2-dicarboxylate (500 mg, 2.15 mmol) were dissolved in DMF (5 mL). CuI (27.5 mg, 0.14 mmol) and K3PO4 (609.3 mg, 2.87 mmol) were added and purged with N2, cyclohexane-1,3-diamine (32.8 mg, 0.29 mmol) was added and the reaction mixture was stirred at 110 C. for 16 h. The reaction mixture was filtered through a pad of diatomaceous earth and the pad was washed with EtOAc (20 mL*3). The filtrate was concentrated under reduced pressure to afford a crude produce as a brown oil. The crude product was purified by column chromatography over silica gel (petroleum ether/ethyl acetate=100:0 to petroleum ether/ethyl acetate=50:50), and the solvents were removed under reduced pressure to afford compound 66a as a brown oil (0.3 g, 58%). LCMS (ESI): m/z 383.0 [M+H]+.

76982-23-5 5-Bromoquinoxaline 610437, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Quinoxaline – Wikipedia
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