Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 82782-85-2, name is Methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate, 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 82782-85-2, category: esters-buliding-blocks

2.5. Synthesis of methyl 2-methyl-4H-furo[3,2-b]pyrrole-5-carboxylate Under N2, to 9 mL of glacial acetic acid were added N,N-dimethylamine (40% aqueous solution) (437 mg, 9.94 mmol), formaldehyde (37% aqueous solution) (283 mg, 9.90 mmol), and methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate (1.64 g, 9.94 mmol). The temperature was kept between 0 and 5 C. while the components were added. The reaction mixture was heated at reflux for 1 h, and was then allowed to stand at rt for 12 h. The mixture was poured onto 30 g of ice, and it was brought to pH 10 by careful addition of 10% sodium hydroxide. The temperature was not allowed to exceed 10 C. while the base was added. The gummy substance solidified when stored in the refrigerator overnight. The solid was collected and dried in vacuo. It was recrystallized from petroleum ether (30-60 C.) to yield methyl 2-[(dimethylamino)methyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (0.80 g, 36%). 1H NMR (400 MHz, CDCl3) delta ppm 2.36 (s, 6H) 3.71 (s, 2H) 3.81 (s, 3H) 6.33 (s, 1H) 6.69 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SEPRACOR INC.; US2008/4327; (2008); A1;,
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Related Products of 455-68-5,Some common heterocyclic compound, 455-68-5, name is Methyl 3-fluorobenzoate, molecular formula is C8H7FO2, 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.

General procedure: Different substituted carboxylic acids (20 mmol) (A) were stirred with thionyl chloride (100 mmol) in dry methanol (75 ml) or 5?6 h to synthesize corresponding methyl esters (B) (Scheme1). After extraction of esters in chloroform, solvent was evaporated and esters (66 mmol) were refluxed with hydrazine hydrate(330 mmol) in ethanol (75 ml) for 4?5 h. A solid was obtained upon removal of the solvent by rotary evaporation. The resulting solid was washed with hexane to afford hydrazide ligand (C). The spectral and analytical data are given below.

The synthetic route of 455-68-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ain, Qurrat Ul; Ashiq, Uzma; Jamal, Rifat Ara; Mahrooof-Tahir, Mohammad; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 115; (2013); p. 683 – 689;,
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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. 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 4-amino-2-methoxybenzoate

Method 2A mixture of methyl 4-amino-2-methoxybenzoate (10.8 g, 59.6 mmol), the product from step(i) above (20.09 g, 54.2 mmol) and potassium carbonate (15 g, 109 mmol) in DMF (300 mL)was degassed with N2 for 10 mm. BrettPhos G3 precatalyst(1 g, 1.103 mmol) was added andthe mixture heated at 85°C for 3 h. The mixture was cooled then partitioned between DCM(500 mL) and water (800 mL). The organic layer was washed with water (500 mL), dried (MgSO4), filtered and evaporated under reduced pressure. The residue was triturated with ether, filtered and dried to afford the sub-title compound (21.7 g) as a grey solid. 1H NMR (400 MHz, DMSO-d6) O 9.38 (s, IH), 9.36 (s, IH), 8.18 (d, IH), 8.14 (d, IH), 7.83 (d,IH), 7.54-7.66 (m, 5H), 7.38 (d, IH), 7.22 (dd, IH), 6.69 (dd, IH), 6.14 (d, IH), 3.74 (s, 3H),3.71 (s, 3H), 1.53 (s, 9H).LCMS m/z 516 (M+H) (ES)

The synthetic route of 27492-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESPIVERT LIMITED; TOPIVERT PHARMA LIMITED; FYFE, Matthew Colin Thor; (62 pag.)WO2016/51188; (2016); A1;,
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Application of 57486-68-7, 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 57486-68-7 as follows.

General procedure: General synthetic procedure for the key lactone intermediates II (6a-6k), for example 6a.2-(O-tolyl) acetic acid (0.15 g, 1 mmol) was dissolved in 15 mL of methanol, slowly add 2-3 drops ofconcentrated sulfuric acid, then refluxing for 8 h and monitored by TLC, after the reaction is completed,the solvent methanol was removed by rotary evaporation, 30 mL of water was added to the residueand stirred, extracted three times with ethyl acetate, washed with water, dried and concentrated to givecompound 5a. The obtained compound 5a was placed in a round bottom flask, and 1.2 eq of methylglycolate, 20 mL of tetrahydrofuran, and 2.2 eq of potassium t-butoxide were added, refluxing andstirring the reaction and monitored by TLC, after the reaction is completed, 50 mL of water was addedto the residue and stirred, adjust the pH of the solution to 5-6, then extracted three times with ethylacetate, washed with water, dried and concentrated to obtain key lactone intermediates II (6a)

According to the analysis of related databases, 57486-68-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bao, Longzhu; Wang, Shuangshuang; Song, Di; Wang, Jingjing; Cao, Xiufang; Ke, Shaoyong; Molecules; vol. 24; 7; (2019);,
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Reference of 5445-17-0, These common heterocyclic compound, 5445-17-0, name is Methyl 2-bromopropanoate, 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 dry 10 mL schlenk flask was added 72.0 mg (0.4 mmol) of 1,1-diphenylethylene,Methyl-2-bromopropionate (99.6 mg, 0.6 mmol)Silver oxide (9.3 mg, 0.04 mmol)Tert-butyl peroxide 72.0 mg (0.8 mmol)Triethylamine 80.8 mg (0.8 mmol)N, N-dimethylacetamide (2 mL),The reaction flask was stirred at 80 C for 24 h under argon atmosphere.After the reaction is complete,The reaction solution was washed with saturated brine,Ethyl acetate extraction (3 x 10 mL),Collecting organic phase,And dried over anhydrous magnesium sulfate.The organic solvent was removed by rotary evaporation,The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate)To give the title product (2-methyl-4,4-diphenylbut-3-enoic acid methyl ester)Yellow oily liquid,Yield 92%.

Statistics shows that Methyl 2-bromopropanoate is playing an increasingly important role. we look forward to future research findings about 5445-17-0.

Reference:
Patent; Ningbo University; Huang Huiyan; Wei Wenting; Zhu Wenming; Ying Weiwei; Zhao Chuanli; Yang Chenguang; Chen Weidong; (6 pag.)CN106892818; (2017); A;,
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369-26-6, name is Methyl 3-amino-4-fluorobenzoate, 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: Methyl 3-amino-4-fluorobenzoate

POCI3 (44 mu, 0.470 mmol) was added to methyl 3-amino-4-fluorobenzoate (53.0 mg, 0.313 mmol) and 4-ethylbenzoic acid (47.0 mg, 0.313 mmol) in MeCN (2 ml) and the mixture was heated at 100 °C for 30 min. Solvents were evaporated and residue purified by flash chromatography using 10-20percent) EtOAc in hexanes. Yield: 18.5 mg (20percent>); white solid. The amide from above (18.5 mg, 0.061 mmol) and Lawesson’s reagent (32 mg, 0.078 mmol) in toluene (2 ml) was heated at 110 °C for 2 d. Solvent was evaporated and residue purified by flash chromatography using 20-35percent EtOAc in hexanes as eluent. Yield: 7.1 mg (39percent). Hydroxylamine potassium salt in MeOH (ca 1.7 M, 1.5 ml) was added to the ester from above and the mixture was heated at 60 °C for 45 min before quenched with AcOH (0.5 ml). The title compound was isolated by reversed phase chromatography (Kinetex CI 8, 5 muiotaeta, 21.2 x 100 mm, flow 25 ml/min, gradient 0.1percent TFA in water / acetonitrile over 15 minutes). Yield; 5.1 mg (72percent); white solid.

The synthetic route of 369-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KANCERA AB; HAMMER, Kristin; JOeNSSON, Mattias; KRUeGER, Lars; (230 pag.)WO2017/108282; (2017); A1;,
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Reference of 25081-39-4,Some common heterocyclic compound, 25081-39-4, name is Methyl 3,5-dimethylbenzoate, molecular formula is C10H12O2, 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.

3.71 g (0.0304 mol) of 2,4-dimethylphenol was dissolved in 111.40 g of toluene,Then 0.22g (0.00304mol) of n-butylamine was added and reacted at 110 C for 4h.Add 5.00g (0.0304mol) to the reaction solutionMethyl 3,5-dimethylbenzoate,Incubation reaction for 6h;After the reaction solution was cooled to 50 C, the pH of the reaction solution was adjusted to 6-7 with 5 wt% H2SO4.Then the reaction solution was washed three times with 30 mL of water, and toluene was distilled off under reduced pressure.The residue in the kettle was recrystallized with 100 mL of methanol.Gives a white solid,The target product yield was 80%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3,5-dimethylbenzoate, its application will become more common.

Reference:
Patent; Tianjin Li’anlong New Materials Co., Ltd.; Li’anlong (Zhongwei) New Materials Co., Ltd.; Tian Jun; Gou Shaoping; Li Dapeng; Zhang Huijing; Fan Xiaopeng; Sun Chunguang; Sun Donghui; Xiong Changwu; Bi Zuopeng; Li Haiping; (8 pag.)CN110407690; (2019); A;,
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Synthetic Route of 23426-63-3, 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 23426-63-3 as follows.

To a 20-L reactor containing dimethyl formamide (4.5 L) was charged 5-methyl-4-nitro- lH-pyrazole la (1.5 kg, 1.0 equiv). The solution was cooled to 0 C and charged with finely ground K2CO3 (2.45 kg, 1.5 equiv) in three portions over ~l h. Methyl 2-bromo-2- methylpropanoate (3.2 kg, 1.5 equiv) was added dropwise to the mixture and then was allowed to warm to ~25 C. The reaction mixture was maintained for 16 h and then quenched with water (15 L) and product was extracted with ethyl acetate. The combined organic layer was washed with water, and then with a brine. The organic layer was dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure to give a light yellow solid. The crude product was purified by crystallization with petroleum ether (15 L), filtered, and dried to give methyl 2- m ethyl -2-(3 -methyl -4-nitro- l//-pyrazol- l -yl)propanoate 3a (2.25 kg, >99% purity by HPLC, 84 % yield) as an off-white solid. NMR (400 MHz, CDCb) 8.28 (s, 1H), 3.74 (s, 3H), 2.53 (s, 3H), 1.85 (s, 6H).

According to the analysis of related databases, 23426-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DENALI THERAPEUTICS INC.; REMARCHUK, Travis; SUDHAKAR, Anantha; (28 pag.)WO2019/126383; (2019); A1;,
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Synthetic Route of 24812-89-3,Some common heterocyclic compound, 24812-89-3, name is Methyl 3-amino-2,4-dimethylbenzoate, molecular formula is C10H13NO2, 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.

Scheme 26, step A. To a solution of 5-bromo-2-(trifluoromethyl)benzoic acid(1.00 g, 0. 00371 mol) in CH2Ch (15 mL) at room temperature are added methyl4-amino-3,5-dimethylbenzoate (0.46 g, 0.00260 mol, see preparation 12) and triethylamine (1.10 ml, 0.00743 mol). After stirring the reaction mixture for 10 minutes, 1-propanephosphonic acid cyclic anhydride (50% solution in ethyl acetate, 6.00 ml,0.00929 mol) is added via syringe and stirred at room temperature. After 14 hours, thereaction mixture is diluted with water and extracted with dichloromethane. The organic layers are combined and dried over magnesium sulfate, filtered, and concentrated underreduced pressure. The resulting residue is purified by flash chromatography (silica gel)with 10-15% EtOAc to give the title compound as an off-white solid (0.45 g, 27.67 %).Mass spectrum (m/z): 430.0 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-2,4-dimethylbenzoate, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; BLANCO-PILLADO, Maria-Jesus; VETMAN, Tatiana Natali; FISHER, Matthew Joseph; KUKLISH, Steven Lee; WO2014/4230; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 107582-20-7, name is Methyl 2,3-diaminobenzoate, 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 107582-20-7, COA of Formula: C8H10N2O2

2-Acetoxymethyl-1H-benzoimidazole-4-carboxylic acid methyl ester To a mixture of 2,3-diamino-benzoic acid methyl ester (40.8 mmol) and diisopropylethyl amine (8.5 mL, 49.0 mmol) in dichloromethane (80 mL) at -30 C. was added dropwise a solution of acetoxy acetyl chloride (4.8 mL, 44.9 mmol) in DCM (15 mL). The mixture was allowed to warm to room temperature and stirred overnight. The mixture was quenched with satd. ammonium chloride (50 mL), the layers separated and the aqueous phase extracted with DCM (60 mL). The combined organic layers were washed with brine and dried (MgSO4). The residue after concentration was dissolved in acetic acid (50 mL) and heated at 100 C. for 30 min. The solution was concentrated and purified by flash chromatography (eluent DCM-ethyl acetate 3:1, 2:1, 1:1) to give 2-acetoxymethyl-1H-benzoimidazole-4-carboxylic acid methyl ester (7.3 g, 72% yield over 2 steps) as an off-white solid. 1H NMR (DMSO-d6) delta: 2.11 (s, 3H), 3.96 (s, 3H), 5.31 (s, 2H), 7.32 (t, J=7.9 Hz, 1H), 7.85 (d, J=7.6 Hz, 1H), 7.93 (d, J=7.9 Hz, 1H); MS m/e 249 (MH+).

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; Yu, Kuo-Long; Wang, Xiangdong; Sun, Yaxiong; Cianci, Christopher; Thuring, Jan Willem; Combrink, Keith; Meanwell, Nicholas; Zhang, Yi; Civiello, Rita L.; US2003/207868; (2003); A1;,
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Ester – an overview | ScienceDirect Topics