Category: 135484-83-2

Application of 135484-83-2,Some common heterocyclic compound, 135484-83-2, name is Methyl 2-amino-4-bromobenzoate, molecular formula is C8H8BrNO2, 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 toluene 12mL solution of methyl 2-amino-4-bromobenzoate 1.2g were added 1-fluoro-4-iodobenzene 1.5mL, cesium carbonate 3.4g, palladium acetate 12mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 32mg at room temperature, and it was heated and refluxed under nitrogen atmosphere for 12 hours. After the reaction mixture was cooled to room temperature, palladium acetate 12mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 32mg were added to it, and it was heated and refluxed under nitrogen atmosphere for 12 hours. After the reaction mixture was cooled to room temperature, water was added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with 1.0mol/L hydrochloric acid and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B (spherical type), eluent; hexane:ethyl acetate=10:1] to give methyl 4-bromo-2-(4-fluoroanilino)benzoate 0.20g of pale yellow solid. 1H-NMR(DMSO-d6) delta value: 3.86(3H,s),6.94(1H,dd,J=8.6,1.7Hz),7.04(1H,d,J=1.7Hz),7 .24-7.35(4H,m),7.80(1H,d,J=8.6Hz),9.27(1H,s).

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

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; EP1860098; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 135484-83-2, name is Methyl 2-amino-4-bromobenzoate, 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. COA of Formula: C8H8BrNO2

B. Ethyl-2-Bromo-3-benzenepropanoate To a solution of compound A (18 g, 79 mmol) and dimethylformamide (55 mg, 0.75 mmol) in dichloromethane (160 mL) cooled to 5 C. was added a solution of oxalyl chloride (80 mL, 2M in dichloromethane). After stirring for thirty minutes at 5 C., the solution was warmed to room temperature and stirred for an additional two hours. Ethanol (100 mL, absolute) was added slowly to the solution and after 15 minutes, the mixture was heated to reflux and held there for two hours. The ethanol was removed by distillation and the desired product was isolated by vacuum distillation (107-115 C. at 0.5 mm Hg) as a colorless oil (12.63 g, 49 mmol, 62%).

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

Reference:
Patent; E. R. Squibb & Sons, Inc.; US5225408; (1993); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 135484-83-2, 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. 135484-83-2, name is Methyl 2-amino-4-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl 2-amino-4-bromobenzoate (15 g, 65 mmol) in trifluoroacetic acid (75 mL) and concentrated HC1 (15 mL) was cooled in an ice water bath. To it sodium nitrite (9.0 g, 130 mmol) in water (15 mL) was added via addition funnel over 15 mm. The reaction stirred at 0 C for 30 mm. Then sodium azide (13 g, 196 mmol) was slowly addedportion-wise. The reaction was stirred at 0 C to rt for 1.5 hrs. The solvents were removed and H20 and EtOAc were added. The layers were separated and the organic layer was washed with saturated NaHCO3 three times and dried over Na2SO4. The solvent was removed and the crude material was purified by chromatography thru a Si02 using a solvent gradient of 100 % Hx to 20 % EtOAc / Hx to afford the title compound (16 g, 61mmol, 95 %). ?H NMR (400 MHz, CDC13) oe ppm 7.74 (d, J 8.4 Hz, 1H), 7.38 (d, J 1.8 Hz, 1H), 7.34 – 7.29 (m, 1H), 3.90 (s, 3H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; EXELIXIS PATENT COMPANY LLC; KICK, Ellen, K.; BODAS, Mandar; MOHAN, Raju; BUSCH, Brett, B.; AVERBUJ, Claudia; VALENTE, Meriah; WURTZ, Nicholas; RAO, Prasanna Savanor, Maddu; SHETTY, Jeevanprakash; VENU, Alla; WO2014/152738; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 135484-83-2,Some common heterocyclic compound, 135484-83-2, name is Methyl 2-amino-4-bromobenzoate, molecular formula is C8H8BrNO2, 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 toluene 12mL solution of methyl 2-amino-4-bromobenzoate 1.2g were added 1-fluoro-4-iodobenzene 1.5mL, cesium carbonate 3.4g, palladium acetate 12mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 32mg at room temperature, and it was heated and refluxed under nitrogen atmosphere for 12 hours. After the reaction mixture was cooled to room temperature, palladium acetate 12mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 32mg were added to it, and it was heated and refluxed under nitrogen atmosphere for 12 hours. After the reaction mixture was cooled to room temperature, water was added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with 1.0mol/L hydrochloric acid and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B (spherical type), eluent; hexane:ethyl acetate=10:1] to give methyl 4-bromo-2-(4-fluoroanilino)benzoate 0.20g of pale yellow solid. 1H-NMR(DMSO-d6) delta value: 3.86(3H,s),6.94(1H,dd,J=8.6,1.7Hz),7.04(1H,d,J=1.7Hz),7 .24-7.35(4H,m),7.80(1H,d,J=8.6Hz),9.27(1H,s).

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

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; EP1860098; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 135484-83-2, 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. 135484-83-2, name is Methyl 2-amino-4-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00404] Step A: Methyl 2-amino-4-bromobenzoate was prepared from the corresponding acid by Fischer esterification. A mixture of methyl 2-amino-4- bromobenzoate (1.1 g, 4.8 mmol) and ethyl carbonocyanidate (0.95 g, 9.66 mmol) in HOAc (4 mL) was treated with a sl2 N HCl (0.4 mL) and the resulting mixture was stirred at 700C for 3 h. After cooling to rt, water was added followed by addition of aq sodium hydrogen carbonate to pH ~5. The precipitated solid was filtered and washed thoroughly with water and diethyl ether to afford ethyl 7-bromo-4-oxo-3,4- dihydroquinazoline-2-carboxylate (825 mg, 58%). 1H NMR (300 MHz, DMSO-d6) delta 12.82 (s, IH), 8.06-8.09 (m, 2H), 7.81 (d, J= 8.4 Hz, IH), 4.38 (q, J= 7.0 Hz, 2H), 1.35 (t, J= 7.0 Hz, 3H); LC-MS (ESI) m/z 296 (M+H)+.

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, Methyl 2-amino-4-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; LIU, Gang; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ABRAHAM, Sunny; SETTI, Eduardo; WO2010/99379; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 135484-83-2, 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. 135484-83-2 name is Methyl 2-amino-4-bromobenzoate, 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 16a4-Bromo-2-(2,5-dichloro-pyrimidin-4-ylamino)-benzoic acid methyl ester2-Amino-4-bromo-benzoic acid methyl ester (1.2g, 5.0 mmol) was combined with2,4,5-trichloro-pyrimidine (5.33 mL, 46.5 mmol) and EtN(i-Pr)2 (0.95 mL, 5.5 mmol), and the mixture was warmed to 120C. After 16 hours the excess 2,4,5-trichloro-pyrimidine was removed under high vacuum, and the residue was then treated with 1 : 1 MeOH: water. The resulting solid was filtered, retriturated with 1 : 1 MeOH: water, re filtered, and the resulting solid triturated in MeOH at 50C. After filtering, the solid was rinsed liberally with MeOH. After air drying 4-Bromo-2-(2,5-dichloro-pyrimidin-4-ylamino)-benzoic acid methyl ester was recovered in 52% yield as a brown solid and was carried on for subsequent steps without further manipulation. LC/MS: M+H= 377.9.

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

Reference:
Patent; CEPHALON, INC.; BRESLIN, Henry J.; DORSEY, Bruce; OTT, Gregory R.; WO2012/125603; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 135484-83-2, name is Methyl 2-amino-4-bromobenzoate, molecular formula is C8H8BrNO2, 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: 135484-83-2

Into a 1000-mE 3-necked round-bottom flask, was placed methyl 2-amino-4-bromobenzoate (5.0 g, 21.73 mmol, 1.00 equiv), a solution of sulfuric acid (20%) (20 mE) in water (100 mE). This was followed by the addition of a solution of NaNO2 (1.8 g, 26.09 mmol, 1.20 equiv) in water (20 mE) dropwise with stirring at 00 C., after stirred 1 hour at 00 C. To this was added a solution of iodopotassium (7.21 g, 43.43 mmol, 2.00 equiv) in water (30 mE) dropwise with stirring at 00 C. The resulting solution was stirred for 1 hour at 00 C. in a water/ice bath. The reaction was then quenched by the addition of 200 mE of water/ice. The resulting solution was extracted with ethyl acetate (100 mEx3) and the organic layers combined. The resulting mixture was washed with brine (100 mExl). The residue was applied onto a silica gel colunm with ethyl acetate/petroleum ether (1/5). This resulted in 5.97 g (81%) of methyl 4-bromo-2-iodobenzoate as light yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 135484-83-2, its application will become more common.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Dong, Hanqing; Homberger, Keith R.; Qian, Yimin; Snyder, Lawrence B.; Wang, Jing; Zimmermann, Kurt; (504 pag.)US2018/215731; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 135484-83-2, name is Methyl 2-amino-4-bromobenzoate, belongs to esters-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 135484-83-2, Recommanded Product: Methyl 2-amino-4-bromobenzoate

Step 3. Preparation of Methyl 4-bromo-2-isopropoxycarbonylaminobenzoate Add isopropyl chloroformate (104 mL, 104 mmol, 1.0 M in toluene) dropwise to a solution of methyl 2-amino-4-bromobenzoate (14.5 g, 63.0 mmol) and pyridine (10.3 mL, 126.0 mmol) in dichloromethane (210 mL) at room temperature under nitrogen and stir for 5.5 h. Pour the reaction into water (500 mL) and separate the layers. Extract the aqueous layer with dichloromethane (2 x 100 mL) and combine the organic extracts and wash with 2 N HCI, saturated sodium bicarbonate and brine (100 mL each), then dry over sodium sulfate, filter and remove the solvent under reduced pressure to afford the title compound as a pale orange solid (19.2 g, 96%)

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, Methyl 2-amino-4-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/37796; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics