Tag: M.W=200-300

1215205-50-7, name is Ethyl 1-(4-bromophenyl)cyclopropanecarboxylate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C12H13BrO2

Example 30 1-(1-{4-[1-(Ethoxycarbonyl)cyclopropyl]benzoyl}piperidin-4-yl)-3-methylpiperidine trifluoroacetic acid salt 600 mg (2.2 mmol) of ethyl 1-(4-bromophenyl)cyclopropanecarboxylate, 813 mg (4.5 mmol) of 4-(3-methylpiperidin-1-yl)piperidine, 294 mg (1.12 mmol) of molybdenum hexacarbonyl, 105 mg (0.11 mmol) of trans-bis(acetate)bis[o-(di-o-tolylphosphine)benzyl]dipalladium(II) (Herrmann’s palladacycle) and 709 mg (6.7 mmol) of sodium carbonate were suspended in 3 ml of water and heated in a microwave at 150 C. for 10 minutes. After cooling, the mixture was extracted with ethyl acetate and then filtered. The organic phase was removed from the filtrate, dried over magnesium sulphate and filtered, and the filtrate was concentrated. The residue was purified by preparative HPLC. [Reprosil C18, 10 mum, 250 mm*30 mm (50% methanol/50% water (+0.05% trifluoroacetic acid) to 70% methanol/30% water (+0.05% trifluoroacetic acid)) over a run time of 25 min]. The product-containing fractions were combined, concentrated and dried under HV. This gave 348 mg (30% of theory) of an oil. LC-MS [Method 2]: Rt=0.74 min; MS (ESIpos): m/z=399 (M-CF3COOH+H)+ 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=0.88-0.94 (m, 3H), 1.11 (t, 3H), 1.20-1.26 (m, 2H), 1.49-1.55 (m, 2H), 1.59-2.19 (m, 8H), 2.58-3.14 (m, 5H), 3.33-3.55 (m, 3H), 3.58-3.88 (m, 1H), 4.04 (q, 2H), 4.29-4.81 (m, 1H), 7.32-7.38 (m, 2H), 7.39-7.43 (m, 2H), 8.98-9.38 (m, 1H)

The synthetic route of 1215205-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; BECKER-PELSTER, Eva Maria; BUCHGRABER, Philipp; BUCHMUeLLER, Anja; ENGEL, Karen; GNOTH, Mark Jean; HIMMEL, Herbert; KAST, Raimund; KELDENICH, Joerg; KLAR, Juergen; KNORR, Andreas; LANG, Dieter; LINDNER, Niels; SCHMECK, Carsten; SCHOHE-LOOP, Rudolf; TINEL, Hanna; TRUeBEL, Hubert; WUNDER, Frank; (97 pag.)US2016/318866; (2016); A1;,
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These common heterocyclic compound, 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, 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. Formula: C9H9BrO3

Step B 2-Bromo-5-methoxybenzyl alcohol Lithium aluminum hydride (1.3 eq) was added in portions to a solution of methyl 2-bromo-5-methoxy benzoate (1 eq) in diethyl ether (0.35 M) at 0 C. under N2 and the resulting mixture allowed to warm to RT with stirring for 5 h. Quenched with H2O (3*g LAH), followed sequentially by 15% NaOH solution (3*g LAH), a nd H2O (3*g LAH). The solution was filtered through a scintered glass funnel rinsing with diethyl ether and concentrated in vacuo to give 2-bromo-5-methoxybenzyl alcohol as a clear oil. EI-MS m/z 239, 241 (M+Na)+

The synthetic route of Methyl 2-bromo-5-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; US6514964; (2003); B1;,
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Adding a certain compound to certain chemical reactions, such as: 107947-17-1, name is Methyl 3-bromo-4-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 107947-17-1, category: esters-buliding-blocks

The compound methyl 4-chloro-3-bromobenzoate 19b (1.2 g, 4.8 mmol), trimethylsilylacetylene (0.95 g, 9.7 mmol), palladium acetate (108 mg, 0.48 mmol), triphenylphosphine (254 mg, 0.97 mmol), cuprous iodide (185 mg, 0.97 mmol) and triethylamine (25 mL) were mixed in a sealed tube, and heated and stirred at 100 C. for 15 hours, after the reaction is completed, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=10/1), so as to obtain the title product methyl 4-chloro-3-((trimethylsilyl)ethynyl)benzoate 19c (1 g, yellow solid), and the yield was 78%. 1H NMR (400 MHz, CDCl3) delta 8.19 (d, J=2.0 Hz, 1H), 7.91 (dd, J=8.4, 2.1 Hz, 1H), 7.48 (d, J=8.4 Hz, 1H), 3.94 (s, 3H), 0.30 (s, 9H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BEIJING INNOCARE PHARMA TECH CO., LTD.; Chen, Xiangyang; Gao, Yingxiang; Kong, Norman Xianglong; (59 pag.)US2019/210997; (2019); 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. 1130165-74-0, name is Ethyl 4-bromo-3-fluorobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 1130165-74-0

Preparation Example 20 A mixture of ethyl 4-bromo-3-fluorobenzoate (1 g), cyclopropylboronic acid monohydrate (643 mg), tetrakistriphenylphosphinepalladium (235 mg), potassium phosphate (3.1 g), toluene (10 ml), and water (1 ml) was thoroughly stirred at 110 C. overnight. To the reaction mixture was added water, followed by carrying out a separation of the layers using ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was crudely purified by silica gel column chromatography (hexane:ethyl acetate=85:15), and then to a mixture of the crude product, THF (20 ml), and MeOH (20 ml) was added a 1 M aqueous sodium hydroxide solution (20 ml), followed by stirring at room temperature overnight. To the reaction mixture was added 1 M hydrochloric acid (20 ml), followed by concentrating under reduced pressure to remove the organic solvent. The precipitated solid was collected by filtration to obtain 600 mg of 4-cyclopropyl-3-fluorobenzoic acid as a colorless solid.

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:
Patent; ASTELLAS PHARMA INC.; US2012/46292; (2012); 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. 1186-73-8, name is Trimethyl methanetricarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Trimethyl methanetricarboxylate

A mixture of N-benzyl-2-(3,6-dihydro-2H-pyran-4-yl)-7-isopropyl-3-(3-methoxypropoxy)-7,8-dihydrooxepino[3,2-b]pyridin-9(6H)-imine (600 mg, 1.29 mmol), trimethylmethanetricarboxylate (491 mg, 2.58 mmol) in Ph20 (3 mL) was degassed under vacuum and purged with nitrogen gas (cycle repeated 3 times). The mixture was stirred at 220 C for 15 min under nitrogen atmosphere. The mixture was cooled to rt and purified directly by normal phase S1O2 chromatography (0-50% EtO Ac/petroleum ether) to give methyl 11-benzyl-2-(3,6-dihydro-2H-pyran-4-yl)-8-hydroxy-7-isopropyl-3-(3-methoxypropoxy)-10-oxo-6,7,10,11-tetrahydrooxepino[3,2-b:4,5-b’]dipyridine-9-carboxylate as a yellow oil (430 mg, 56% yield, m/z: 591 [M+H] observed).

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:
Patent; ARBUTUS BIOPHARMA, INC.; CHEN, Shuai; DORSEY, Bruce D.; FAN, Yi; GOTCHEV, Dimitar B.; QUINTERO, Jorge; (252 pag.)WO2019/177937; (2019); 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. 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C8H6BrFO2

2,6-dimethyl-4-(methylsulfonyl)phenol (0.307 g, 1.533 mmol), methyl 3-bromo-4-fluorobenzoate (0.375 g, 1.609 mmol) and cesium carbonate (0.749 g, 2.299 mmol) werecombined in dimethyl sulfoxide (1.533 mL) under argon in a sealed tube and heated at100 C for 24 hours. The mixture was partitioned between water and ethyl acetate. Theorganic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification of the resulting residue by chromatography (silica, 20-40 % of 3:1 ethyl acetate/ethanol in heptanes) provided material that was 80-90 % pure. This material was triturated in 1:1 ethyl acetate/heptane to provide the title compound (0.29 g, 44 %).

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:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; HASVOLD, Lisa A.; LIU, Dachun; MCDANIEL, Keith F.; PRATT, John; SCHRIMPF, Michael; SHEPPARD, George S.; WANG, Le; LI, Bing; (191 pag.)WO2017/177955; (2017); A1;,
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Reference of 252881-74-6, 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 252881-74-6 as follows.

SI- 16 (202 mg, 0.69 mmol, 1.2 eq.), COMU (296 mg, 0.69 mmol, 1.2 eq.), and N- methylmorpholine (190 pL, 1.7 mmol, 3 eq.) were dissolved in 1.5 mL DMF and incubated for 1 min. Amino-PEG3-t-butyl ester (160 mg, 0.58 mmol, 1 eq.) was added in 2.5 mL DMF and the reaction was stirred for 2h. The reaction was diluted with ethyl acetate (15 mL) and acidified with 1N HC1 to pH 3. The organic layer was washed with water (3x 25 mL) and brine (25 mL), dried over anhydrous MgS04, and concentrated under reduced pressure. The resulting residue was purified by flash chromatography to provide the title compound as a colorless oil (215 mg, 57%). NMR (500 MHz, Chloroform-if) d 7.66 (d, j= 8.7 Hz, 2H), 7.33 (d, j= 8.7 Hz, 2H), 6.97 (dd, J= 8.8, 7.2 Hz, 4H), 6.82 (d, J= 5.4 Hz, 1H), 3.63 (t, J= 6.5 Hz, 2H), 3.62 – 3.57 (m, 10H), 3.54 (td, J= 4.8, 4.4, 1.1 Hz, 2H), 2.43 (t, J= 6.5 Hz, 2H), 1.39 (s, 9H). HRMS (ESI) [M+H]+ for CieHseBrNiOe 551.1751, found 551.1751.

According to the analysis of related databases, 252881-74-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; ZHANG, Xiaoyu; CROWLEY, Vincent; CRAVATT, Benjamin; (121 pag.)WO2020/77278; (2020); A1;,
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110661-91-1, name is tert-Butyl 4-bromobutanoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: tert-Butyl 4-bromobutanoate

Intermediate 6 (10.47 g, 11.73 mmol) was dissolved in acetonitrile (500 ml) and tert-butyl bromoacetate (10.0 g, 44.84 mmol) and DIPEA (9.08 mg, 70.38 mmol) were added. The reaction mixture was stirred at RT for 14 days and then filtered. Evaporation of the solvent gave crude product which was purified using a Combiflash companion (120 g cartridge) eluting with 0-10% MeOH in DCM. The solid product was triturated with Et2O to give a white solid. Yield: 8.79 g (72%) LC-MS (Method 2): Rt = 2.93 min, m/z = 1036 [M+H]+

The synthetic route of 110661-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; WO2009/60206; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 4841-22-9, name is Methyl 2-(4-chlorophenoxy)acetate, molecular formula is C9H9ClO3, 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. Application In Synthesis of Methyl 2-(4-chlorophenoxy)acetate

To the obtained methyl 4-chlorophenoxyacetate, 401.74 g of 25% sulfuric acid was added, and the acid hydrolysis reaction was carried out at 80 C for 2 h.At the same time, the alcohol formed by the reaction is distilled off, and the reaction is cooled to room temperature and filtered.The filter cake was washed with a small amount of water, and the filter cake was dried to obtain 182.27 g of 4-chlorophenoxyacetic acid.The content was 98.6%, and the total yield was 96.31% based on phenol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4841-22-9, its application will become more common.

Reference:
Patent; Shandong Runbo Biological Technology Co., Ltd.; Sun Guoqing; Hou Yongsheng; Chi Zhilong; Zhang Liguo; Hu Yishan; (13 pag.)CN108947839; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 39149-80-9, name is tert-Butyl 2-bromopropanoate, 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 39149-80-9, Product Details of 39149-80-9

Sodium hydride (60% dispersion in mineral oil) (1.02 g, 25.43 mmol) was added to a solution of methyl 2-(2-bromo-4-fluorophenyl)acetate (5.24 g, 21.19 mmol) and 1,3- dimethyl-3,4,5,6-tetrahyaYo-2(lH)-pyrimidinone (2.56 mL, 21.19 mmol) in anhydrous THF (50 mL). The reaction mixture was stirred for 15 min. before a solution of tert-butyl- 2-bromopropionate (5.32 g, 25.43 mmol) in anhydrous THF (5 mL) was added to it. The reaction mixture was stirred at room temperature overnight. The reaction mixture was heated to 60C for a further 24 h. After that time, the mixture was cooled to room temperature and poured onto water. The mixture was extracted with EtOAc and the combined organic layers were washed with brine, dried (Na2S04), filtered and concentrated in vacuo. The crude material was purified by column chromatography on silica, eluted with 10% EtOAc/hexane to afford the title compound. (0689) ?H NMR (400 MHz, CDCb) 8ppm 0.87 – 1.01 (m, 2 H), 1.19 (s, 4 H), 1.23 – 1.29 (m, 1 H), 1.46 (s, 5 H), 2.92 – 3.23 (m, 1 H), 3.55 – 3.72 (m, 3 H), 4.29 – 4.46 (m, 1 H), 6.94 – 7.07 (m, 1 H), 7.26 – 7.49 (m, 2 H)

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; LIWICKI, Gemma; MACK, Stephen; STEPHENSON, Anne; TEALL, Martin; WHITE, Kathryn; (168 pag.)WO2018/47983; (2018); A1;,
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