Category: 55687-02-0

55687-02-0, 6-Bromo-2-chloroquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of tert-butyl (2S)-2-[5-(2-chloropyrimidin-5-yl)-1 H-imidazol-2-yl]pyrrolidine-1-carboxylate (0.11 g, 0.33 mmol), obtained from Preparation 101 , in dry dioxane (2 mL), was added hexamethylditin (0.11 g, 0.33 mmol), followed by Pd(PPh3)4 (0.095 g, 0.082 mmol). The reaction mixture was degassed and then heated to reflux for 2 hours. After this time, it was cooled to room temperature and diluted with ethyl acetate (20 ml_). The organic phase was washed with saturated ammonium chloride solution (20 ml_), water (20 ml_) and brine (20 ml_); then dried over anhydrous sodium sulphate, filtered and the solvent was removed in vacuo. The residue was dissolved in DMF (2 ml_) and 6-bromo-2-chloroquinoxaline (0.088 g, 0.33 mmol), obtained from Preparation 30, was added, followed by cesium fluoride (0.09 g, 0.59 mmol), copper (I) chloride (0.033 g, 0.33 mmol) and Pd(PPh3)4 (0.095 g, 0.082 mmol). The reaction mixture was degassed and stirred at 1100C for 3.5 hours. It was then allowed to cool to room temperature and was diluted with ethyl acetate (20 ml_). The resulting suspension was washed with 0.88 ammonia solution (50 ml_) and the aqueous phase was back extracted with more ethyl acetate (4 x 20 ml_). The combined organic phases were dried over anhydrous sodium sulphate, filtered and the solvent was removed in vacuo. The crude material was purified by chromatography on silica gel (ethyl acetate: heptane 1 :5 to 1 :1 to ethyl acetate: methanol 95:5) to afford the title compound as a bright yellow solid (80 mg).LCMS (run time = 4.5 min): Rt = 2.76 min; m/z 522; 524 [M+H]+., 55687-02-0

The synthetic route of 55687-02-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PFIZER LIMITED; MILBANK, Jared Bruce John; PRYDE, David Cameron; TRAN, Thien Duc; WO2011/4276; (2011); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

55687-02-0, 6-Bromo-2-chloroquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6-bromo, 2-chloroquinoxaline (0.700 g, 2.8 mmol) and Triethylamine (0.87 g, 8.6 mmol) were dissolved in DMSO (15 mL) at room temperature and (f?)-1-(3-Fluoro-phenyl)- ethylamine hydrochloride (0.400 g, 2.8 mmol) was added. The reaction mixture was stirred at RT for 16 hours. After completion of reaction (confirmed by TLC), water (10OmL) was added to the reaction mixture and it was extracted with ethyl acetate (50 mL x 3). The organic layer was washed with water (15 mL), brine (15 mL), and was then dried over Na2SO4. The organic layer was concentrated in vacuo to afford the crude product.The crude product was adsorbed on silica gel and was purified by column chromatography using neutral silica gel of 60-120 mesh size. Methanol (1-1.5 %) was used as a gradient in DCM for elution of the title compound as a solid (0.35 g, 36%)., 55687-02-0

The synthetic route of 55687-02-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SENTINEL ONCOLOGY LIMITED; BOYLE, Robert, George; WALKER, David, Winter; WO2010/136755; (2010); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55687-02-0,6-Bromo-2-chloroquinoxaline,as a common compound, the synthetic route is as follows.

The title compound was prepared from 6-Bromo-2-chloro-quinoxaline (3 g, 12.32 mmol) using the method applied for example 5 with the following exceptions: (1 ) in step 1 , 1-Methyl-1-phenyl-ethylamine (1.99 g, 14.72 mmol) was used instead of (R)-1 -(3-Fluoro-phenyl)-ethylamine and Nu,Nu-Diisopropylethylamine (8.4 mL, 6.23 g, 48.23 mmol) was used instead of trimethylamine (2) Title product was isolated as the free base. Yield of final step: 0.04 g (41 %)., 55687-02-0

The synthetic route of 55687-02-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SENTINEL ONCOLOGY LIMITED; BOYLE, Robert George; WALKER, David Winter; (166 pag.)WO2016/170163; (2016); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

55687-02-0,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55687-02-0,6-Bromo-2-chloroquinoxaline,as a common compound, the synthetic route is as follows.

Methyl (S)-1-((S)-2-(5-(4-(6-bromoquinoxalin-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate A mixture of methyl (S)-3-methyl-1-oxo-1-((S)-2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate (5 g, 10.1 mmol), 6-bromo-2-chloroquinoxaline (2.94 g, 12.1 mmol), cesium carbonate (6.51 g, 20.1 mmol), dioxane (100 mL) and water (10 mL) was degassed and flashed with nitrogen three times. Tetrakis(triphenylphosphine)palladium (0) (1.16 g, 1.01 mmol) was then added to the mixture. The mixture was then heated at 80 C. overnight while stirring. Solvent was then removed by evaporation in vacuo. The solid residue was treated with DCM and water to make a biphasic solution. The dichloromethane layer was separated, dried over sodium sulfate, filtered and evaporated. The black crude product was purified by column (0-5% MeOH in DCM) to give a deep colored solid product, methyl (S)-1-((S)-2-(5-(4-(6-bromoquinoxalin-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (5.47 g, 94%): ESI-LRMS m/e calcd for C28H29BrN6O3 [M+] 578, found 579 [M+H+].

The synthetic route of 55687-02-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Alam, Muzaffar; Berthel, Steven Joseph; Brinkman, John A.; Hawley, Ronald Charles; Li, Hongju; Palmer, Wylie Solang; Pietranico-Cole, Sherrie; Sarabu, Ramakanth; Smith, Mark; So, Sung-Sau; Yi, Lin; Zhai, Yansheng; Zhang, Qiang; Zhao, Shu-Hai; US2012/230951; (2012); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55687-02-0,6-Bromo-2-chloroquinoxaline,as a common compound, the synthetic route is as follows.

55687-02-0, In a 10 ml seal tube, methyl (4S,7S)-6,10-dioxo-4-(5-(4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl)- 1 H-imidazol-2-yl)octahydro- 1 H-pyridazino [ 1 ,2- a][l,2]diazepin-7-ylcarbamate (240 mg, 459 muiotaetaomicron?) (Intermediate 3), 6-bromo-2- chloroquinoxaline (112 mg, 459 muiotaetaomicron?) and Cs2C03 (299 mg, 917 muiotaetaomicron?) were combined with 1,4-dioxane (3.00 ml) and water (0.5 ml) to give a light brown solution. It was degased for 10 min and tetrakis(triphenylphosphine)palladium (0) (53.0 mg, 45.9 muiotaetaomicron?) was added. The reaction mixture was heated at 80 C for 16 h. It was diluted with EtOAc (6 ml) andconcentrated in vacuo. The residue was purified on a silica gel column (CH2C12, 2%, 3%, 5%, 8% and 10% MeOH/CH2Cl2 ) to afford methyl (4S,7S)-4-(5-(4-(6-bromoquinoxalin-2- yl)phenyl)- 1 H-imidazol-2-yl)-6, 10-dioxooctahydro- 1 H-pyridazino [ 1 ,2-a] [ 1 ,2]diazepin-7- ylcarbamate as a red solid (240 mg, 86.6%). ESI-LRMS m/e calcd for C28H26BrN704 [M+] 604, found 605 [M+H+].

As the paragraph descriping shows that 55687-02-0 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; BRINKMAN, John A.; LI, Hongju; SARABU, Ramakanth; SO, Sung-Sau; WO2013/53657; (2013); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55687-02-0,6-Bromo-2-chloroquinoxaline,as a common compound, the synthetic route is as follows.

55687-02-0, To a stirred suspension of (2-[(2S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]-1-{[2 (trimethylsilyl) ethoxy]methyl}- 1 H-imidazol-5-yl)boronic acid (150 mg, 0.26 mmol), obtained from Preparation 13b, in 1 ,2-dimethoxyethane (1 mL), was added 6-bromo-2-chloroquinoxaline (62 mg, 0.26 mmol), obtained from Preparation 30,Pd(dppf)CI2.DCM (13 mg, 0.05mmol) and 2M Na2CO3 (aq) (0.38 mL, 0.77 mmol). The mixture was degassed, then put under nitrogen three times and then stirred at 300C for 3 hours. The resulting dark brown mixture was partitioned between ethyl acetate (5 mL) and water (5 mL). The organic phases were extracted and the aqueous phase was washed with more EtOAc (5 mL). The organic phases were combined, dried (Na2SO4), filtered and concentrated in vacuo. The resulting crude material was purified by column chromatography (dry loaded redisep (4 g), 20 to 80 % ethyl acetate, heptane) to give 98 mg of the title compound as a orange foam.1H-NMR (400 MHz, MeOD): delta= 9.28 (1 H, d), 8.22 (1 H, d), 7.95 (3H, m), 6.70 (1 H, m), 5.95 (1 H, dd), 5.16(1 H, m), 3.75-3.52 (4H, m), 2.42 (1 H, m), 2.24-1.91 (3H, m), 1.46-1.21 (9H, m), 0.86 (2H, m), -0.17 (9H, d).LCMS (run time = 6 min): Rt = 4.38 min; m/z 574; 576 [M+H]+

As the paragraph descriping shows that 55687-02-0 is playing an increasingly important role.

Reference£º
Patent; PFIZER LIMITED; MILBANK, Jared Bruce John; PRYDE, David Cameron; TRAN, Thien Duc; WO2011/4276; (2011); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

55687-02-0,55687-02-0, 6-Bromo-2-chloroquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 4 4-(4-((6-Bromo-2-quinoxalinyl)oxy)phenoxy)-2-penten-1-ol STR17 A mixture of 3.76 g (15.4 mmol) of 6-bromo-2-chloroquinoxaline, 3.00 g (15.4 mmol) of 4-(4-hydroxy- phenoxy)-2-penten-1-ol, 2.34 g (16.9 mmol) of powdered, anhydrous potassium carbonate and 50 ml of dry dimethylsulfoxide was stirred at room temperature for a period of 24 hours. The mixture was poured over ice and extracted three times with ether. The combined ether layers were washed with 1 percent aqueous sodium hydroxide, then with water, dried over MgSO4 and evaporated to dryness. The residue was recrystallized from toluene to give 2.50 g of the desired pentenol as a yellow solid. (Compound D).

The synthetic route of 55687-02-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; The Dow Chemical Company; US4900354; (1990); A;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55687-02-0,6-Bromo-2-chloroquinoxaline,as a common compound, the synthetic route is as follows.

A slurry of 5-cyclopropyl-3-(2,6-dichlorophenyl)-4-(7-azaspiro[3.5]non-1-en-2-yl)isoxazole (25 mg, 0.07 mmol, synthesis described in General Method A), 6-bromo-2-chloroquinoxaline (19.5 mg, 0.08 mmol) and Cs2CO3 (43.4 mg, 0.13 mmol) in dioxane (0.3 mL) was degassed by bubbling nitrogen through the mixture for 5 minutes. Chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) (RuPhos-Pd-G2) (2.59 mg, 3.33 mumol) was added and the reaction mixture was sealed and heated to 90C. for 6 hours. The crude reaction mixture purified directly by flash chromatography on SiO2 (0-100% EtOAc/hexanes, Isco 12 g column) to yield 4-(7-(6-bromoquinoxalin-2-yl)-7-azaspiro[3.5]non-1-en-2-yl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazole (26 mg, 0.04 mmol, 64% yield) as a gum. 1H NMR (400 MHz, CDCl3) delta 8.57 (s, 1H), 8.03 (d, J=2.2 Hz, 1H), 7.64 (dd, J=8.8, 2.2 Hz, 1H), 7.53 (d, J=8.8 Hz, 1H), 7.46-7.42 (m, 2H), 7.40-7.34 (m, 1H), 5.80 (s, 1H), 3.94 (dt, J=13.5, 5.1Hz, 2H), 3.66-3.50 (m, 2H), 2.44 (s, 2H), 2.21 (tt, J=8.4, 5.1Hz, 1H), 1.76 (t, J=5.6 Hz, 4H), 1.36-1.30 (m, 2H), 1.22-1.15 (m, 2H)., 55687-02-0

Big data shows that 55687-02-0 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; Carpenter, Joseph E.; Huang, Yanting; Wang, Ying; Wu, Gang; (137 pag.)US2019/127362; (2019); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55687-02-0,6-Bromo-2-chloroquinoxaline,as a common compound, the synthetic route is as follows.

6-bromo-2-chloroquinoxaline (0.365 g 1.5 mmol) was dissolved in DMSO (10 mL) at room temperature and (R)-1-[3-(4-Methyl-piperazin-1-yl)-phenyl]-ethylamine (0.33 g, 1.5 mmol) and triethylamine (0.626 mL, 4.50mmol) were added to the solution. The reaction mixture was stirred at room temperature overnight. After completion of the reaction, water (100 mL) was added and the product was extracted with ethyl acetate (3 x 50 mL). The organic layer was washed with water (10 mL) followed by brine solution (10 mL) and dried over Na2SO4. The organic layer was concentrated in vacuo to afford the crude product.The product was purified by column chromatography using neutral silica gel of 60-120 mesh size and was eluted by a gradient of 5-15 % ethyl acetate in hexane to afford the title compound as a solid (0.250 g, 47%)., 55687-02-0

The synthetic route of 55687-02-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SENTINEL ONCOLOGY LIMITED; BOYLE, Robert, George; WALKER, David, Winter; WO2010/136755; (2010); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

55687-02-0,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55687-02-0,6-Bromo-2-chloroquinoxaline,as a common compound, the synthetic route is as follows.

6-bromo, 2-chloroquinoxaline (0.35 g 1.4 mmol) was dissolved in DMSO (12 ml_) at room temperature and (R)-1-(3-Chloro-phenyl)-ethylamine (0.44 g, 2.8 mmol) was added. The reaction mixture was stirred at RT for 16 hours. After completion of the reaction (confirmed by TLC), water (10OmL) was added to the reaction mixture and it was extracted with ethyl acetate (50 mL x 3). The organic layer was washed with water (15 mL), brine (15 mL), and then dried over Na2SO4. The organic layer was concentrated in vacuo to afford the crude product.The crude product was adsorbed on 60-120 mesh silica gel and purified by column chromatography using neutral silica gel of 60-120 mesh size. A gradient of 0.5 % methanol in DCM was used for elution of the title compound (0.380 g, 72%).

As the paragraph descriping shows that 55687-02-0 is playing an increasingly important role.

Reference£º
Patent; SENTINEL ONCOLOGY LIMITED; BOYLE, Robert, George; WALKER, David, Winter; WO2010/136755; (2010); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider