Category: 59557-91-4

Related Products of 59557-91-4, A common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

Step 4 4-bromo-2-methoxy-5-nitroaniline (compound 12-6) Potassium nitrate (217 mg, 2.25 mmol) was added to a solution of compound 12-5 (400 mg, 2.0 mmol) in 3.5 ml of concentrated sulfuric acid at -20 C., and vigorously stirred at -20 C. for 5 min. After completion of the reaction, the reaction mixture was diluted with water, extracted with EA/water system, washed with water for three times, and dried, and the organic layer was concentrated under reduced pressure to give the crude product compound 12-6 (300 mg) which was used directly in the next step. MS m/z (ESI): 246.9 [M+H]+.

The synthetic route of 59557-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHANGHAI HAIYAN PHARMACEUTICAL TECHNOLOGY CO. LTD.; YANGTZE RIVER PHARMACEUTICAL GROUP CO., LTD.; LAN, Jiong; JIN, Yunzhou; ZHOU, Fusheng; XIE, Jing; SHEN, Sida; HU, Yi; LIU, Wei; LV, Qiang; (96 pag.)US2017/8889; (2017); A1;,
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Reference of 59557-91-4, These common heterocyclic compound, 59557-91-4, name is 4-Bromo-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.

At 5 C., a solution of bromine (9.8 mL, 192.5 mmol, 1.1 eq) in dichloromethane (120 mL) was added slowly to a dichloromethane solution (240 mL) of 4-bromo-2-methoxyaniline (35.35 g, 175 mmol) under vigorous stirring. The reaction mixture was kept at this temperature for 2 h. After the completion monitored by TLC, the reaction mixture was poured into ice water and extracted with ethyl acetate (3*200 mL). The organic layer was combined, washed with brine (3*50 mL) and dried over sodium sulfate. Then the reaction mixture was purified by flash column chromatography (ethyl acetate/hexanes (v/v)=5/95). The product (40.3 g, yield=82%) was obtained as a red liquid. 1H NMR (600 MHz, CDCl3) delta 7.20 (d, J=1.9 Hz, 1H), 6.84 (d, J=1.8 Hz, 1H), 4.21 (s, 2H), 3.86 (s, 3H). LRMS m/z 280.0 [M+H]+.

The synthetic route of 59557-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Regents of the University of Michigan; Cierpicki, Tomasz; Grembecka, Jolanta; Huang, Huang; Zari, Sergi; Cho, Hyo Je; Potopnyk, Mykhaylo; Dudkin, Sergeii; Chen, Wenbing; Adam, Yassir; Howard, Christina; Kim, EunGi; US2019/183865; (2019); A1;,
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Related Products of 59557-91-4, The chemical industry reduces the impact on the environment during synthesis 59557-91-4, name is 4-Bromo-2-methoxyaniline, I believe this compound will play a more active role in future production and life.

A stirred solution of NaNO2 (5.63 g, 81.7 mmol) in conc. HCl (6.2 ml) was cooled to 10 C. 4-bromo-2-methoxy-phenylamine (15 g, 74 mmol) in HOAc (100 ml) was added at such a rate that the temperature of the r.m. was maintained below 10 C. After addition was completed, the mixture was stirred at r.t. for 30 min. This solution was added dropwise, to a stirring solution of KI (37 g, 223 mmol) in 48% HBr (200 ml) at r.t. This mixture was stirred for 1 h and was then diluted with ice water (1000 ml). The resulting white precipitate was collected by filtration and washed with H2O, yielding a solid (a) and the mother liquor (b).The solid (a) was suspended in a mixture of DCM and a sat. aq. Na2CO3 solution. The resulting slurry was filtered over diatomaceous earth. The organic layer of the filtrate was washed with a diluted NH4OH solution until the disappearance of blue colour. The organic phase was dried (MgSO4), filtered and evaporated to yield a brown solid. The mother liquor (b) was basified by the addition of solid Na2CO3 and was then extracted with DCM. The combined organic extracts were washed with a diluted NH4OH solution until the disappearance of blue colour. The organic phase was dried (MgSO4), filtered and evaporated to give a brown solid.The 2 brown solids were combined, yielding 24.0 g of intermediate 54 (91%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Van Brandt, Sven Franciscus Anna; De Cleyn, Michel Anna Jozef; Gijsen, Henricus Jacobus Maria; Berthelot, Didier Jean-Claude; Surkyn, Michel; US2012/295891; (2012); A1;,
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Related Products of 59557-91-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 59557-91-4, name is 4-Bromo-2-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

STEP 2: tert-Butyl 7-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2,3- dihydrobenzoxazepine-4(5H)-carboxylate (500 mg, 2.33 mmol), 4-bromo-2- methoxyaniline (296 mg, 1.47 mmol), potassium carbonate (737 mg, 5.34 mmol) and [l,r-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (97.5 mg, 0.13 mmol) were heated at HO0C in DME (7 mL) and water (1 mL) over 48 h. The mixture was then cooled to room temperature and diluted with an excess of ethyl acetate and filtered through a bed of celite. The filtrate was partitioned with water and the organic phase washed with brine and dried over anhydrous sodium sulfate. The mixture was filtered and concentrated and the residue purified by silica chromatography using 85:15 hexanes: ethyl acetate as eluent to give 1,1-dimethylethyl 7-[4-amino-3- (methyloxy)phenyl]-2,3-dihydro-l,4-benzoxazepine-4(5H)-carboxylate (198 mg, 40%). MS (EI) C2IH26N2O4: 371 (MH+).

The synthetic route of 4-Bromo-2-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; ANAND, Neel, Kumar; BAIK, Tae-Gon; BLAZEY, Charles, M.; BUSSENIUS, Joerg; CURTIS, Jeffry, Kimo; DEFINA, Steven, Charles; DUBENKO, Larisa; HARRIS, Jason, R.; JACKSON-UGUETO, Eileen; JOSHI, Anagha; KIM, Angie, Inyoung; MANALO, Jean-Claire, Limun; PETO, Csaba, J.; RICE, Kenneth, D.; TSANG, Tsze, H.; WO2010/135568; (2010); A1;,
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Related Products of 59557-91-4, These common heterocyclic compound, 59557-91-4, name is 4-Bromo-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.

A mixture of 4-bromo-2-methoxyaniline (208 mg, 1.03 mmol), 1 ,2,4-triazole (80 mg, 1.13 mmol), Cs2CO3 (0.67 g, 2.06 mmol) and Cul (20 mg, 0.103 mmol) in DMF was heated at 110 oC for 20 h. Further portions of 1,2,4-triazole (0.1 g, 1.44 mmol), Cs2CO3 (0.67 g, 2.06 mmol) and Cul (0.1 g, 0.52 mmol) were added and the mixturewas heated a further 72 h at 110 oC. The mixture was cooled, diluted with ethyl acetate (20 mL) and washed with water (2 x 20 mL). The combined aqueous washes were reextracted with ethyl acetate (20 mL). The combined organics were passed through a phase separation cartridge and the solvent removed under reduced pressure. Purification of the residue via silica gel column chromatography (0-100% ethyl acetate isohexane)gave 2-methoxy-4-(1H-1,2,4-triazol-1-yl)aniline as a light red solid (92 mg, 47%). ?H NMR (400 MHz, CDC13): oe 8.41 (s, 1H); 8.05 (s, 1H); 7.11 (d, J = 2.3, 1H); 6.99 (dd, J = 8.3, 2.3, 1H); 6.74 (d, J = 8.3, 1H); 3.97 (s, 2H); 3.92 (s, 3H).

The synthetic route of 59557-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BAKER-GLENN, Charles; CHAMBERS, Mark; CHAN, Bryan K.; ESTRADA, Anthony; SWEENEY, Zachary Kevin; WO2013/79495; (2013); A1;,
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Synthetic Route of 59557-91-4,Some common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

4-Bromo-2-methoxyaniline (50.0 g, 247 mmol) was added to a mixture of sodium 3- nitrobenzenesulfonate (86.8 g, 385 mmol) and propane-1 ,2,3-triol (108 g, 1 .18 mol) in cone. H2SO4 (97 ml.) and water (75.7 ml.) at 0 C over a period of 30 min under nitrogen. After stirring at 120 C for 24 h and then cooling to RT, the reaction mixture was quenched slowly with 2M NaOH (1 L). The aq. solution was extracted with EtOAc (3 x 500 ml_). The combined organic phases were dried over Na2S04, filtered and concentrated to afford 6-bromo-8- methoxyquinoline (Intermediate 49, 60.0 g, 100%); M/Z (ES+), [M+H]+= 237.1H NMR (300 MHz, DMSO-ofe) delta 3.99 (s, 3H), 7.30 (d, 1 H), 7.58-7.60 (m, 1 H), 7.79 (s, 1 H), 8.28 (dd, 1 H), 8.86 (dd, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-methoxyaniline, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; PACKER, Martin, John; PERKINS, David, Robert; SWALLOW, Steven; HIRD, Alexander; YE, Qing; PENG, Bo; ZHENG, Xiaolan; JOHANNES, Jeffrey; MLYNARSKI, Scott; LAMB, Michelle; HUYNH, Hoan; ROBBINS, Daniel, William; (182 pag.)WO2018/178226; (2018); A1;,
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Synthetic Route of 59557-91-4, The chemical industry reduces the impact on the environment during synthesis 59557-91-4, name is 4-Bromo-2-methoxyaniline, I believe this compound will play a more active role in future production and life.

4-(Dipropylphosphoryl)-2-methoxyaniline To a solution of 4-bromo-2-methoxyaniline (0.100 g, 0.495 mmol) in 2 mL DMF was added dipropylphosphine oxide (0.0730 g, 0.544 mmol), palladium acetate (5.6 mg, 0.025 mmol), XANTPHOS (17.2 mg, 0.030 mmol), and potassium phosphate (0.116 g, 0.544 mmol). The mixture was purged with nitrogen, and subjected to microwaves at 150 C. for 20 minutes. The reaction mixture was concentrated and purified by silica gel chromatography (0-12% 7N ammonia in methanol:dichloromethane) and the fractions were concentrated. The residue was acidified with 2.5 M HCl in ethanol and the solution was concentrated to provide 4-(dipropylphosphoryl)-2-methoxyaniline as the hydrochloride salt (0.132 g, 91% yield).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; Wang, Yihan; Huang, Wei-Sheng; Liu, Shuangying; Shakespeare, William C.; Thomas, Ranny M.; Qi, Jiwei; Li, Feng; Zhu, Xiaotian; Kohlmann, Anna; Dalgarno, David C.; Romero, Jan Antoinette C.; Zou, Dong; US2015/225436; (2015); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 59557-91-4, name is 4-Bromo-2-methoxyaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 59557-91-4

General procedure: 4-Bromobenzenamines 1a-c (6.4 mmol) were dissolved in the mixed solvents (2M K2CO3:DMF = 1:1, 24 mL), and then added corresponding 4-substituent phenylboronic acids 2a-h (7.7 mmol) and Pd (PPh3)4 (0.22 mmol) under argon. The reaction mixture was refluxed at 100 for 15 h (TLC monitored the reaction). The reaction was then cooled to room temperature and filtered. The filtrate was added 10 times the amount of water and extracted with ethyl acetate. The organic layer was washed with saturated NaCl solution, concentrated under reduced pressure, and dried to give a crude product. The crude product was purified by flash column chromatography (ethyl acetate/petroleum ether, 1:8-1:5) to afford 1,1′-biphenyl-4-amines 3a-x, yield: 77-95%.

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:
Article; Liu, Jingru; Ma, Ruxin; Bi, Fangchao; Zhang, Fa; Hu, Chaoyu; Venter, Henrietta; Semple, Susan J.; Ma, Shutao; Bioorganic and Medicinal Chemistry Letters; vol. 28; 10; (2018); p. 1825 – 1831;,
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Related Products of 59557-91-4, 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. 59557-91-4 name is 4-Bromo-2-methoxyaniline, 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.

Example 62 5-(2,3-dichlorobenzyl)-7-{ [2-methoxy-4-(piperidin-4-yl)phenyl]amino} [l ,2,4]triazolo[4,3- c]pyrimidine-8-carboxamide Example 62A feri-butyl 4-(4-amino-3-methoxyphenyl)-5,6-dihydropyridine-l(2//)-carboxylate A mixture of 4-bromo-2-methoxybenzenamine (1.21 g, 6.0 mmol), tert-butyl 4- (3,3,4,4-tetramethylborolan-l -yl)-5,6-dihydropyridine-l (2//)-carboxylate (1.95 g, 6.3 mmol), sodium carbonate (1 .91 g, 18 mmol) and 1 , 1 ‘- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.22 g, 0.3 mmol) in dioxane (25 mL) and water (5 mL) was degassed with nitrogen and heated to 90C for 15 hours. After cooling to ambient temperature, the mixutre was filtered, concentrated and purified by flash chromatography eluting with 200: 1 dichloromethane:methanol to give the title compound. MS: 305 (M+Hf).

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

Adding a certain compound to certain chemical reactions, such as: 59557-91-4, name is 4-Bromo-2-methoxyaniline, 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 59557-91-4, name: 4-Bromo-2-methoxyaniline

A mixture of Example 175A (36.4 g, 180 mmol), and di-tert-butyl dicarbonate (47.2 g, 216 mmol) in THF (500 mL) was heated to reflux for 20 hours and cooled to ambient temperature. HPLC (using the conditions from Example 175A, product Rt=13.55 min and TLC (8:2 heptane/ethyl acetate, Rf of product=0.53, Rf of 4-bromo-2-methoxyaniline=0.27) indicated approximately 10% starting material was remaining. Additional di-tert-butyl dicarbonate (3.9 g, 18 mmol) was added and heating was continued for another 5 hours. The mixture was cooled and evaporated under reduced pressure. The residue was applied to a 400 gram silica gel column and eluted with 8:2 heptane/ethyl acetate. The fractions showing the desired product were combined and washed with saturated NaHCO3 and then brine. The organic solution was dried (MgSO4), filtered, and concentrated to provide 61.3 g of a mixture of the desired product and di-tert-butyl dicarbonate which was used directly in the next step

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