Tag: M.W=200-300

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.

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:
Patent; Zhejiang University of Technology; Ruisheng Optoelectric Science And Technology (Changzhou) Co., Ltd.; Li Guijie; Huang Da; Chen Shaohai; (53 pag.)CN109678907; (2019); A;,
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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. 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C11H14ClNO2

To a solution of (3R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1 .0]hexane-3- carboxylic acid (syn-anti diastereoisomer mixture 10/2) (D27) (3.06 g, 13.5 mmol) in dry DMF (15 ml) under N2 atmosphere HOBT.H20 (2.06 g, 13.46 mmol), EDC.HCI (3.87 g, 20.20 mmol), methyl 4-(1 -aminocyclopropyl)benzoate hydrochloride (3.06 g, 13.46 mmol) and TEA (4.7 ml, 33.7 mmol) were added in sequence. The mixture was stirred for 2 hrs at RT, then the solvent was evaporated in vacuo and the residue taken up in AcOEt (500ml), washed twice with water (50 ml), dried over Na2SO4 and evaporated to afford a residue which was loaded on a SNAP-Si cartridge (100g) and eluted with a mixture DCM/AcOEt from 10/0 to 9/1 . Collected fractions after solvent evaporation afforded the two diastereoisomer (D73a) (2.55 g) and (D73b) (880 mg). (D73a) (syn diastereoisomer) MS: (ES/+) m/z: 401 .4 [MH+] C22H28N2O5 requires 400.20 1 H NMR (400 MHz, DMSO-d6) delta (ppm): 8.70 (s, 1 H), 7.90 – 7.76 (m, 2 H), 7.34 – 7.19 (m, 2 H), 4.52 – 4.35 (m, 1 H), 3.84 (s, 3 H), 3.43 – 3.32 (m, 1 H), 2.67 -2.39 (m, 1 H), 1 .88 – 1 .74 (m, 1 H), 1 .52 – 1 .33 (m, 10 H), 1 .27 – 1 .12 (m, 4 H), 1 .09 – 0.92 (m, 1 H), 0.66 – 0.53 (m, 1 H). (D73b) (anti diastereoisomer) MS: (ES/+) m/z: 401 .4 [MH+] C22H28N2O5 requires 400.20 1 H NMR (400 MHz, DMSO-d6) delta (ppm): 8.69 – 8.52 (s, 1 H), 7.90 – 7.73 (m, 2 H), 7.35 – 7.19 (m, 2 H), 3.93 – 3.75 (m, 4 H), 3.36 – 3.30 (m, 1 H), 2.35 – 2.19 (m, 1 H), 2.12 – 2.02 (m, 1 H), 1 .90 – 1 .74 (m, 1 H), 1 .47 – 1 .30 (m, 9 H), 1 .25 – 1 .07 (m, 4 H), 0.73 (td, J = 5.4, 8.8 Hz, 1 H), 0.39 (br. s., 1 H).

The synthetic route of 1014645-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; PUCCI, Sabrina; STASI, Luigi, Piero; ROVATI, Lucio; WO2013/4290; (2013); A1;,
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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 7459-46-3 as follows. category: esters-buliding-blocks

To a solution of compound 30 (495 g, 2.01 mol) in tert-butanol (4 L) was added NaBH4 (434 g, 12.04 mol) with vigorous stirring at RT under N2 atmosphere. To this stirred solution was added methanol (250 mL) in three portions during 45 mins maintaining a gentle reflux. The reaction mixture was slowly warmed to 80 °C and allowed to reflux at the same temperature for over night. The reaction mixture was cooled, added 5M hydrochloric acid to get pH = 7 (app). The mixture was filtered, the residue washed with ethanol (2 x 500 mL) and combined the organic layers. The solvent was removed under vacuum and the crude product was purified by column chromatography on silica gel (10percent methanol in chloroform) to give the title compound (160 g, 66percent). TLC: Chloroform/Methanol, 4: 1, Rf=0.2

According to the analysis of related databases, 7459-46-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEDIVIR AB; WO2005/65689; (2005); A1;,
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Synthetic Route of 2672-58-4,Some common heterocyclic compound, 2672-58-4, name is Trimethyl benzene-1,3,5-tricarboxylate, molecular formula is C12H12O6, 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 solution of Trimethyl 1,3,5-Benzenetricarboxylate (1.1 g, 4.36 mmol) in MeOH (100 mL) wasadded 1 M NaOH aq. (3.95 mL, 3.95 mmol). The solution was stirred for 22 h at rt. After removal ofthe solvent by evaporation, the mixture was washed with CH2Cl2. The aqueous layer was acidified with 6 M HCl to pH 2 and then extracted with AcOEt. The organic layer was dried over Na2SO4 andthe solution was concentrated by evaporation to give 17 (849 mg, 79%) as a white solid.

The synthetic route of 2672-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zenmyo, Naoki; Tokumaru, Hiroki; Uchinomiya, Shohei; Fuchida, Hirokazu; Tabata, Shigekazu; Hamachi, Itaru; Shigemoto, Ryuichi; Ojida, Akio; Bulletin of the Chemical Society of Japan; vol. 92; 5; (2019); p. 995 – 1000;,
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Synthetic Route of 35450-36-3, 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. 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of Cs2CO3 (2 mmol) in H2O (5 mL) were added methyl 2-bromobenzoate (1a, 1 mmol), 1H-pyrazol-5-amine (2a, 1.2 mmol), and CuI (0.2 mmol). The mixture was stirred at 100 C under nitrogen atomasphere until a complete conversion as indicated by TLC. It was cooled to room temperature and then extracted with ethyl acetate. The combined organic phase was dried over anhydrous Na2SO4, and concentrated under vacuum. The crude product was purified by column chromatography eluting with petroleum ether/ethyl acetate (3:1) to give 3a. Products 3b-3t and 6 were obtained in a similar manner.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-5-methoxybenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Xinying; Gao, Lin; Wang, Zhangxin; Fan, Xuesen; Synthetic Communications; vol. 45; 21; (2015); p. 2426 – 2435;,
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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. 27007-53-0, name is Methyl 2-bromo-5-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 2-bromo-5-chlorobenzoate

To a stirred solution of methyl 2-bromo-5-chlorobenzoate (10 g, 40.1 mmol) in 1,4-dioxane (50 mL) cooled to -10 C. was added bis(pinacolato)diboron (12.21 g, 48.1 mmol) and PdCl2(dppf) (1.466 g, 2.004 mmol) followed by potassium acetate (11.80 g, 120 mmol). The mixture was then heated to 90 C. overnight. The reaction mixture was cooled to room temperature, diluted with water (300 mL) and extracted with ethyl acetate (500 mL). The organic layer was separated and dried over sodium sulphate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10% ethyl acetate in petroleum ether) to afford methyl 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (11.8 g, 39.8 mmol, 99% yield). LC/MS (ESI) m/e 297.2 [(M+H)+, calcd for C14H19BClO4, 297.1]; LC/MS retention time (Method A1): tR=2.32 min; 1H NMR (400 MHz, CHLOROFORM-d) delta 7.92 (d, J=2.0 Hz, 1H), 7.49 (dd, J=8.0, 2.0 Hz, 1H), 7.45-7.41 (m, 1H), 3.92 (s, 3H), 1.41 (s, 12H).

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 27007-53-0.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Nara, Susheel Jethanand; Dzierba, Carolyn Diane; Macor, John E.; Bronson, Joanne J.; Ramkumar, Rajamani; Maishal, Tarun Kumar; Karatholuvhu, Maheswaran Sivasamban; Thangavel, Soodamani; Thiyagarajan, Kamalraj; (77 pag.)US2018/141956; (2018); A1;,
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Related Products of 57486-69-8, 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 57486-69-8 as follows.

Methyl o-bromophenylacetate (4.6g, 0.02mol),2,6-Dichloroaniline (16.4 g, 0.1 mol),Copper iodide (1.92g, 0.01mol),Anhydrous potassium carbonate (11.2g, 0.08mol) and xylene (100ml) were placed in a dry reaction flask.Under nitrogen protection,The reaction was stirred at 200C for 50 hours under reflux.Activated carbon is added after the reaction is completed.Hot filter,The filtrate was concentrated to dryness under reduced pressure.The residue is dissolved in methanol,Crystallize in ice water bath,Suction filtrationWhite solid 5.50g (diclofenac methyl ester) was dried,Yield 87.8%.

According to the analysis of related databases, 57486-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Huazhong University of Science and Technology; Zhu Dajian; Li Tao; Chen Jian; Bi Jiajun; Meng Di; (7 pag.)CN107793323; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 685892-23-3, name is Methyl 2-bromo-6-chlorobenzoate, 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 685892-23-3, category: esters-buliding-blocks

Step 1. Preparation of methyl 2-chloro-6-(4.4.5.5-tetramethyl-1.3.2-dioxaborolan-2-yl)benzoate (i-5a) [00144] To a solution of methyl 2-bromo-6-chlorobenzoate (7.50 g, 30.1 mmol) in dioxane (65 mL) was added Bis(pinacolato)diboron (15.3 g, 60.3 mmol), AcOK (3.54 g, 36.1 mmol) and PdCl2(dppf) (0.66 g, 0.90 mmol) under N2 atmosphere, then the resulting mixture was stirred at 100 C for 18 h, cooled to room temperature, filtered and concentrated, the residue was purified by chromatography (0-3% EtOAc in petroleum ether) to give the title compound. MS: 297 (M+l). XH NMR (400 MHz, CDC13) delta 7.67 (d, J = 7.4 Hz, 1H), 7.46 (d, J = 7.8 Hz, 1H), 7.29-7.39 (m, 1H), 3.92 (s, 3H), 1.32 (s, 12H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-bromo-6-chlorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LAPOINTE, Blair, T.; FULLER, Peter, H.; GUNAYDIN, Hakan; LIU, Kun; SCOTT, Mark, E.; TROTTER, B., Wesley; ZHANG, Hongjun; (211 pag.)WO2017/75182; (2017); A1;,
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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. 55666-43-8, name is tert-Butyl 3-bromopropanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: tert-Butyl 3-bromopropanoate

Sodium Hydride (60% dispersion in mineral oil, 10. [1G,] 0.252 mol) was added portionwise to a stirred solution of [2-OXAZOLIDINONE] (20g, 0.23 mol) in dry tetrahydrofuran [(250ML)] at 0 [C] under nitrogen. After stirring for 30 minutes tert-butyl bromoacetate (50.8 [MI,] 0. [344MOL)] was added slowly and the reaction mixture was left heating to room temperature and stirred overnight. Water was then slowly added followed by ethyl acetate [(250ML).] The aqueous phase was extracted and washed with ethyl acetate [(50ML).] The combined organic phases were washed with brine [(200ML),] dried over magnesium sulphate and concentrated under vacuum. The title compound crystallized on standing as a white solid (45g, 97%). ‘H-NMR (400 MHz, [CDC13)] : [8=] 1.46 (s, 9H), 3.68 (t, 2H), 3.91 (s, 2H), 4.36 (t, 2H

The synthetic route of 55666-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/16583; (2004); A1;,
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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 619-42-1 as follows. COA of Formula: C8H7BrO2

Step 1 Synthesis of 4-Phenylamino-benzoic acid methyl ester A mixture of Pd(OAc)2 (5 mg, 0.02 mmol), dicyclohexylphosphino-2′,3′-dimethoxy biphenyl (17 mg, 0.04 mmol) in toluene (20 mL) was purged with argon gas for 10 minutes, To the resulting mixture was added, aniline (136 mg, 1.46 mmol) and K3PO4(136 mg, 1.46 mmol) and purged with argon gas for 10 minutes and to which added 4-bromobenzoicacid methyl ester (300 mg, 1.4 mmol) and heated to reflux overnight. The reaction mixture was diluted with ethyl acetate and filtered the residue; the filtrate collected was concentrated under reduced pressure to afford the crude mass. The resultant mass was purified by column chromatography (using 60-120 silica gel and 10% EtOAc in Hexane as eluent) to afford 201 mg (63.4%) of 4-Phenylamino-benzoic acid methyl ester.

According to the analysis of related databases, 619-42-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bischoff, Alexander; Subramanya, Hosahalli; Sundaresan, Kumar; Sammeta, Srinivasa Raju; Vaka, Anil Kumar; US2010/160323; (2010); A1;,
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