52727-57-8 Archives - Esters-buliding-blocks

Sep-21 News Discovery of 52727-57-8

The synthetic route of 52727-57-8 has been constantly updated, and we look forward to future research findings.

Application of 52727-57-8, These common heterocyclic compound, 52727-57-8, name is Methyl 2-amino-5-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.

Example 88:Methyl 2-amino-5-[4-(methylsulfonyImethyl)-6-morpholin-4-yl-pyrimidin-2- yljbenzoateA mixture of methyl-2-amino-5-bromobenzoate (250 mg), potassium acetate (320 mg) and bis(pinacolato)diboron (332 mg) in 1,4-dioxane (10 mL) was degassed for 5 minutes. 1,1′- Bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane adduct (54 mg) was added and the reaction was heated to 8O0C for 2.5 hours. 2-Chloro-4-(methylsulfonylmethyl)-6-mophiholin-4-yl-pyrimidine (381 mg), ethanol (0.75 mL), a 2M solution of sodium carbonate (2.7 mL) and additional 1,1′- bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane adduct (54 mg) were added and the heating was continued for a further 3.5 hours. The cooled reaction mixture was loaded on a SCX-2 (10 g), removed with 7N ammonia in methanol and the solution concentrated in vacuo. The residue was chromatographed on silica, eluting with 50% ethyl acetate in DCM, to give the desired material as a yellow solid (82 mg). Mass Spectrum; MH+ 407 NMR Spectrum: 1H NMR (DMSO-d6) 53.22 (3H, s), 3.69 (4H, s), 3.73 (4H, s), 3.84 (3H, s), 4.49 (2H, s), 6.77 (IH, s), 6.87 (IH, d), 7.05 (2H, s), 8.24 (IH, d), 8.79 (IH, s)

The synthetic route of 52727-57-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/80382; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

S News New downstream synthetic route of 52727-57-8

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-5-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Synthetic Route of 52727-57-8, 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. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 1a (18.60 g, 80.85 mmol) was dissolved in concentrated hydrochloric acid (200 mL, 12N), and an aqueous solution of sodium nitrite (6.69 g, 97.02 mmol) was slowly added dropwise at -10 to 0C. The reaction solution was at 0C. Stir for 1 hour. This reaction was added dropwise to a mixture of cuprous chloride (800 mg, 8.09 mmol) and sulfur dioxide (15.54 g, 242.55 mmol) at 0C. The resulting reaction solution was stirred at 0 C. for 1 hour and further warmed to 20 C. and stirred for 3 hours. After the reaction was completed, it was extracted with ethyl acetate (200 mL×3). The organic phases were combined, dried, concentrated to dryness under reduced pressure, and separated and purified by column chromatography on silica gel (petroleum ether/ethyl acetate=100-0%) to give Compound 1b (4.10 g).

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Nanjing Mingde Drug Discovery Co., Ltd.; Yao Yuanshan; Chen Bin; Chen Yuan; Li Ao; Xu Ran; Huang Zhensheng; Tian Dongdong; Li Hongwei; Yang Chengshuai; Li Jian; Chen Shuhui; (26 pag.)CN107987072; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Share a compound : 52727-57-8

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-5-bromobenzoate, its application will become more common.

Reference of 52727-57-8,Some common heterocyclic compound, 52727-57-8, name is Methyl 2-amino-5-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.

3- (morpholin-4-ylsulfonyl) benzoic acid (271 mg, 1.0 mmol) was suspended in [CH2C12] (10 mL) and (COCl) 2 added (725 mg, 5.7 mmol). A catalytic amount [OF DMF] was then added and the mixture stirred for 4 hrs. The solvent was then removed in vacuo to give the acid chloride as an oil. The oil was dissolved in [CHC13] (10 mL). Methyl 2- amino-5-bromobenzoate (230 mg, 1.0 mmol) was added followed by pyridine [(1] mL). The solution was stirred at room temperature for an additional 12 hrs then poured into 1 M HC1 (20 [ML)] and extracted with EtOAc (3 x 20 mL). The combined organic solutions were dried over Na2S04 and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (20% EtOAc in hexane) to provide 367 mg of the desired methyl ester (76%). The ester was treated with [LIOH] in 1: 1: 1 THF/MeOH/H20 for 12 hrs followed by acidification and extraction with EtOAc. The organic solution was dried over NazS04 and then concentrated in vacuo. The title compound (328 mg, 92%, 70% overall) was obtained as a white solid after recrystalization from [MEOH.] H NMR (400 MHz, DMSO) 2.93 (m, [4H),] 3.65 [(M,] 4H), 7.88 (dd, 1H), 7.90 (d, 1H), 8.00 (d, [1H),] 8.13 (d, 1H), 8.25-8. 29 [(M,] [2H),] 8. 59 (d, 1H), 12.21 (s, 1H).

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18414; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Share a compound : C8H8BrNO2

The synthetic route of 52727-57-8 has been constantly updated, and we look forward to future research findings.

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. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

[3-F [ (4-CHLOROPHENYL)] (methyl) amino] [SULFONYL}-2-METHYLBENZOATE] (404 mg, 1.19 mmol) was suspended in dry [CH2C12] (10 mL) and DMF (10 [. L) UNDER N2.] The solution was treated with oxalyl chloride (Aldrich, 0.192 mL, 2.2 mmol) and stirred while gas evolved. After one hour the excess solvent and oxalyl chloride were evaporated and the resultant residue was taken up in dry [CH2C12] (10 mL). [METHYL-2-AMINO-5-] bromobenzoate (Aldrich, 230 mg, 1.0 mmol) was added as a solution in pyridine (3 mL) and the amber solution stirred at RT. After 2 hours [HPLC] indicated the reaction was complete. The mixture was diluted with CH2Cl2 (100 [ML)] and washed 2x with 1. OM HC1 followed by brine (100 mL each). The organic layer was evaporated and purified on a Biotage Flash 25M+ (40 g) silica cartridge using [CH2C12.] The combined fractions were evaporated and the product was dried under vacuum at [100 C] to afford 535mg (97%) of a glass-like [SOLID. 1H NMR] (400 MHz, DMSO-d6) 8 10.88 (s, 1 H), 8.05 (d, J= 8.9 Hz, [1] H), 7.99 (d, J= 2.3 Hz, 1 H), 7.93 (D, J= 7.5 Hz, 1 H), 7.86 (dd, J= 8.8, 2.4 Hz, 1 H), 7.80 (d, J= 7.3 Hz, 1 H), 7.57 (t, J= 7.9 Hz, 1 H), 7.45 (d, [J=8. 7HZ, 2H),] 7.29 (d, [J=8. 7HZ, 2H),] 3.83 (s, [3H),] 3.24 (s, [3H),] 2. [39] (s, [3 H).] 322 mg of the methyl ester solid was dissolved in hot dioxane (10 mL), and after cooling was treated with 1. OM [LIOH] (1.0 [ML,] 1.0 [MMOL).] After stirring overnight at RT the reaction was complete by [HPLC] and OAMS showed correct [M/Z] for the product. The solvent was evaporated and the residue was poured into 1. OM HC1 (100 mL) to afford a white precipitate. The product was extracted into EtOAc (125 [ML)] and washed 3x with [1.] OM HCl, and lx with brine (100 mL each). The organic layer was dried over [NA2S04,] filtered and evaporated to dryness. The crude product was re- [ CRYSTALLIZEDFROMHOTMEOH/ETOH. THERESULTANTPRODUCTWAS DRIEDAT 100 CUNDER] vacuum to afford 213 mg (68%) of white [CRYSTALS. 1H] NMR (400 MHz, DMSO-d6) [B] 11. [35] (s, 1 H), 8. [39] (d, [J=] 8.9 Hz, 1 H), 8.07 (d, [J=] 2.5 Hz, 1 H), 7.92 (dd, [J=] 8.1, 1. [0 HZ, 1 H),] 7.81-7. 89 (m, 2 H), 7.56 (t, [J= 7. 8 HZ, 1 H),] 7.41-7. 48 (m, 2 H), 7.24- 7.34 (m, 2 H), 3.23 (s, 3 H), 2.39 (s, [3 H).]

The synthetic route of 52727-57-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18414; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Introduction of a new synthetic route about 52727-57-8

According to the analysis of related databases, 52727-57-8, the application of this compound in the production field has become more and more popular.

Related Products of 52727-57-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 52727-57-8 as follows.

a) Methyl 2-amino-5-cyanobenzoate b) Methyl 2-amino-3-ethyl-5-cyanobenzoate A mixture of methyl 2-amino-5-bromobenzoate (4.6 g, 20 mmol), and CuCN (1.97 g, 22 mmol) in NMP (20 mL) was heated to 190 C. and 3 h. The reaction mixture was poured into a solution of ethylene diamine 4 mL) in H2O(16 mL) and extracted with toluene (4*20 mL). The extracts were dried (Na2SO4). Removal of the solvent gave the title compound a) (i.e., R8 is hydrogen). Use of methyl 2-amino-5-bromo-3-ethyl bromobenzoate gave the title compound b) (iLe., R8 is ethyl).

According to the analysis of related databases, 52727-57-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bi, Yingzhi; Yu, Guixue; Rotella, David P.; Macor, John E.; US2002/177587; (2002); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Brief introduction of 52727-57-8

Electric Literature of 52727-57-8,Some common heterocyclic compound, 52727-57-8, name is Methyl 2-amino-5-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.

Intermediate 4 (6.90 g, 30 mmol, 1.0 eq.) was added sequentially to a 100 mL dry three-necked flask with a magnetic rotor and a condensing tube.2,5-Dimethylbenzeneboronic acid (3.84 g, 31.5 mmol, 1.05 equivalent),Pd(PPh3)4 (1.04g, 0.9mmol, 0.03 equivalents),K2CO3 (8.29g, 60mmol, 2.0 equivalents),Swap three times with nitrogen, was added 1,4-dioxane (30mL) and H2O (15mL) under nitrogen.The temperature of the oil bath was raised to 100 C and the reaction was stirred for 6.0 hours.After cooling to room temperature, it was extracted three times with 30 mL of ethyl acetate.Then, filtration, distillation under reduced pressure, removal of the solvent, dry-loading, separation and purification using a silica gel column chromatography column, the eluent is petroleum ether / ethyl acetate = 20:1,5.29 g of a white solid were obtained in a yield of 69%. Used directly in the next step.

Reference:
Patent; Zhejiang University of Technology; Ruisheng Optoelectric Science And Technology (Changzhou) Co., Ltd.; Li Guijie; Huang Da; Chen Shaohai; (53 pag.)CN109678907; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Analyzing the synthesis route of 52727-57-8

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 2-amino-5-bromobenzoate

To a solution of compound 28-6 (2.1 g, 9.17 mmol) in THF (20 mL) was added a aqueous solution of NaOH (2.1 g, 20 mL). At the end of the addition, the mixture was stirred at 60 C overnight. After the reaction was completed, the THF solvent was removed. The residue was dissolved in EtOAc (50 mL) and washed with water (50 mL x 3). The combined aqueous phase was adjusted to pH 4 with hydrochloric acid (1 M) and the solid was precipitated. The resulting mixture was filtered to give the title compound as a pale yellow solid (1.42 g, 72%). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) mlz: 217 [M+H] +; and ln NMPv (400 MHz, CDC13) delta (ppm): 7.59 (d, 1H, J= 8.0 Hz), 6.96 (d, 1H, J= 1.6 Hz), 6.64 (dd, 1H, J= 8.0 Hz, 2.0 Hz).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 52727-57-8.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; XIE, Hongming; REN, Qingyun; LI, Shifeng; FU, Changping; HU, Bailin; WU, Xiwei; TANG, Changhua; WO2014/82380; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Discovery of Methyl 2-amino-5-bromobenzoate

The synthetic route of 52727-57-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/80382; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

New downstream synthetic route of Methyl 2-amino-5-bromobenzoate

Related Products of 52727-57-8, 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. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Application of 52727-57-8

Related Products of 52727-57-8, These common heterocyclic compound, 52727-57-8, name is Methyl 2-amino-5-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.

To a mixture of methyl 2-amino-5-bromobenzoate (2.32 g, 10.1 mmol), 4-fluorophenylboronic acid (1.70 g, 12.1 mmol, 1.20 equiv), PdCl2(amphos)2 (79.0 mg, 0.112mmol, 1.1 mol %), and tripotassium phosphate n-hydrate (3.28 g, ca. 12 mmol, ca. 1.2 equiv)were added 1,4-dioxane (40 mL) and H2O (4 mL) at room temperature and the mixture washeated at 100 C with stirring for 16 h. After cooling to room temperature, the mixture wasconcentrated under reduced pressure. The mixture was extracted with EtOAc (10 mL × 3),and the combined organic extract was washed with brine (5 mL), dried (Na2SO4), and, afterfiltration, the filtrate was concentrated under reduced pressure. The residue was purified byrecrystallization from n-hexane to give methyl 2-amino-5-(4-fluorophenyl)benzoate (2.01 g,8.20 mmol, 82.0%) as a pale yellow solid.

Statistics shows that Methyl 2-amino-5-bromobenzoate is playing an increasingly important role. we look forward to future research findings about 52727-57-8.

Reference:
Article; Nakamura, Yu; Yoshida, Suguru; Hosoya, Takamitsu; Chemistry Letters; vol. 46; 6; (2017); p. 858 – 861;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics