Esters-buliding-blocks

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. 1105187-36-7, name is Methyl 3-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 3-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate

Methyl 3-bromo-6-iodo-4H-thieno[3,2-b]pyrrole-5-carboxylate (173 mg, 0.45 mmol), 3-acetamido-phenylboronic acid (80 mg, 0.45 mmol), tetrakis triphenylphosphine palladium (0) (26 mg, 0.02 mmol) and potassium carbonate (0.45 ml, 2M aq. solution, 0.90 mmol) were mixed under nitrogen atmosphere in degassed 1,2-dimethoxyethane (4 mL). The reaction mixture was refluxed overnight. Water (10 mL) was added and the mixture was extracted with ethyl acetate (2×15 mL). After drying with MgSO4, filtering and evaporation of the solvent, the product was purified by silica gel flash chromatography (40% ethyl acetate in iso-hexane) to give the desired product (62 mg, 32% yield). ESI-MS [M+H] 395, 393; 1H NMR (400 MHz, ODd3) O 9.05 (br 5, 1 H), 7.75 (m, 1 H), 7.48 (dm, J = 7.7 Hz, 1 H), 7.39 – 7.29 (m, 2H), 7.20 (brs, 1H), 7.14 (brs, 1H), 3.80 (5, 3H), 2.13 (5, 3H).

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 1105187-36-7.

Reference:
Patent; OXFORD UNIVERSITY INNOVATION LIMITED; GISING, Johan; LINDSTROM, Stefan; ANTONOV, Dmitry; BRANDT, Peter; BELFRAGE, Anna Karin; BREM, Juergen; SCHOFIELD, Christopher J.; (161 pag.)WO2018/215800; (2018); A1;,
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Synthetic Route of 107045-28-3,Some common heterocyclic compound, 107045-28-3, name is tert-Butyl 4-(aminomethyl)benzoate, molecular formula is C12H17NO2, 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.

A solution of 5-bromo-2-iodobenzoic acid (5. 00g, 15. [3MMOL)] in dimethylformamide [(60ML)] was treated with EDAC. [HC1] (3.. [51G, 18. 4MMOL), 1-] [HYDROXYBENZOTRIAZOLE] hydrate (2. [48G,] 18. 4mmol), and 4-aminomethylbenzoic acid tert-butyl ester (3.74g, 18. [4MMOL),] then stirred overnight at room temperature. The solution was treated with water [(40ML),] saturated aqueous sodium bicarbonate solution (15mL), followed by water [(40ML)] and the mixture stirred at room temperature for 1 hour. The solid was collected by filtration, washed with water and allowed to air dry overnight. The solid was heated in hexanes/ethyl acetate 2: 1, cooled to room temperature, and the crystals collected by filtration. Drying afforded the product as 6.30g of white solid (79.8% yield). [1H-NMR] [(CDC13)] ; d 7.98-7. 96 (d, [2H),] 7.70-7. 68 (d, 1H), 7.53-7. 52 (d, [1H),] 7.44-7. 43 (d, [2H),] 7.24-7. 21 (dd, 1H), 6.13 (bs, 1H), 4.67 (d, 2H), 1.60 (s, [9H).] MS: M+ +1 = 515.9/517. 9 Da.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4-(aminomethyl)benzoate, its application will become more common.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/14379; (2004); 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. 178312-47-5, name is Ethyl 4,4-difluorocyclohexanecarboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H14F2O2

Under nitrogen atmosphere, 2.3 g of ethyl 4,4- difluorocyclohexanecarboxylate was dissolved in 50 ml of tetrahydrofuran. Thereto 0.46 g of lithium aluminum hydride was added at 0C and the mixture was stirred at 0C for an hour. Thereafter, 1N aqueous sodium hydroxide was added to the reaction mixture, and formed solids were filtered and then washed with ethyl acetate. The filtrate and the washing solution were combined, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain (4, 4-difluorocyclohexyl) methanol.

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; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2005/63694; (2005); A1;,
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Application of 40872-87-5,Some common heterocyclic compound, 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, molecular formula is C8H8ClNO2, 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 methyl 3-amino-4-chlorobenzoate (3.00 g, 16.2 mmol) and l-(morpholin-4- yl)cyclopropanecarboxylic acid hydrochloride (1:1) (example 65A, 6.71 g, 32.3 mmol, 2 equiv) in DMF (50 mL) was added (benzotriazol-l-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PYBOP, 16.8 g, 32.3 mmol, 2 equiv) and diisopropylethylamine (14.1 mL, 80.8 mmol, 5 equiv). The resulting mixture was stirred at room temperature for 3 days. (Benzotriazol-1- yloxy)tripyrrolidinophosphonium hexafluorophosphate (PYBOP, 16.8 g, 32.3 mmol, 2 equiv) and diisopropylethylamine (14.1 mL, 80.8 mmol, 5 equiv) were added and the resulting mixture was stirred at 60 C over night. The mixture was concentrated under reduced pressure, was then dissolved in dichloromethane, was washed with IN aqueous hydrogen chloride solution and saturated, aqueous sodium bicarbonate solution, was dried over sodium sulfate and concentrated under reduced pressure. The remaining solids were then triturated with ethanol (40 mL), and the resulting mixture was stirred for 30 minutes. The remaining solids were removed by filtration, washed with ethanol, and were dried at 50 C under reduced pressure. The remaining solids were then triturated with ethanol (70 mL), and the resulting mixture was stirred under reflux. After cooling to room temperature, the remaining solids were removed by filtration, washed with ethanol, and were dried at 50 C under reduced pressure to give the title compound (3.60 g). LC-MS (Method 4): Rt= 1.23 min; MS (ESIpos): m/z = 339 [M+H]+.

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-4-chlorobenzoate, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; THEDE, Kai; SCOTT, William Johnston; BENDER, Eckhard; GOLZ, Stefan; HAeGEBARTH, Andrea; LIENAU, Philip; PUEHLER, Florian; BASTING, Daniel; SCHNEIDER, Dirk; MOeWES, Manfred; WO2014/147182; (2014); A2;,
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Related Products of 6279-86-3,Some common heterocyclic compound, 6279-86-3, name is Triethyl methanetricarboxylate, molecular formula is C10H16O6, 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.

Indoline (9a) (1.6 mL, 12.9 mmol) was added dropwise with stirring to triethyl methanetricarboxylate (3.2 mL, 12.9mmol) heated to 215C, at such a rate that the temperature of the reaction mixture was maintained within ¡À5C of the initial temperature. The ethanol eliminated during the reaction was distilled through a suitable still-head. After adding all the indoline the reaction mixture was maintained at the same temperature for 10-15 min, after which it was cooled. The solid ester 5a was filtered off, washed with water, and dried. Yield 1.3 g (38%); mp 303.0 -304C LC-MS (M+1) 260.4 1H NMR (300 MHz, DMSO) delta 13.10 (s, 1H), 7.68 (d, J = 8.2 Hz, 1H), 7.52 (d, J = 7.1 Hz, 1H), 7.22 – 7.13 (m, 1H), 4.33 (q, J = 7.1 Hz, 2H), 4.26 – 4.16 (m, 2H), 3.37 (s, 1H), 3.32 (s, 1H), 1.31 (t, J = 7.1 Hz, 3H).

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

Reference:
Article; Huddar, Srigouri; Jang, Soojin; Kim, Hyung Jun; Lee, Sunkyung; Park, Chul Min; Bioorganic and medicinal chemistry letters; (2020);,
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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. 178312-47-5, name is Ethyl 4,4-difluorocyclohexanecarboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 4,4-difluorocyclohexanecarboxylate

A solution of butyllithium (1.600 mL, 4.00 mmol) was added to cold (- 78 C) solution of diisopropylamine (0.565 mL, 4.00 mmol) in THF (5 mL) under nitrogen and the mixture was stirred at -78 C 1 h. A solution of ethyl 4,4- difluorocyclohexanecarboxylate (384 mg, 2 mmol) in THF (2 mL) was added at – 78 C and the mixture was stirred for 1 h. The mixture was gradually warmed to – 20 C over 2 h and then recooled to – 78 C and connected to a balloon of oxygen and stirred at – 78 C for 1 h. The reaction mixture was added satd. NaHSC solution (5 mL) and allowed to warm to rt and stirred at rt overnight. The reaction mixture was diluted with ether and organic layer separated, washed with water, brine, dried ( a2S04). Evaporation of the solvent afforded a light yellow oil which was purified by silica gel FCC (DCM) to afford ethyl 4,4-difluoro- 1 -hydroxy – cyclohexanecarboxylate as a colorless oil (143 mg). NMR (400MHz,CHLOROFORM-d) delta 4.28 (q, J= 7.3 Hz, 2 H), 2.23 (br. s, 1 H), 2.19 – 1.99 (m, 6 H), 1.83 – 1.73 (m, 2 H), 1.33 (t, J= 1.0 Hz, 3 H).1 N NaOH (0.382 mL, 0.382 mmol) was added to a solution of ethyl 4,4- difluoro-l -hydroxy cyclohexanecarboxylate (26.5 mg, 0.127 mmol) in THF (0.5 mL) and methanol (0.5 mL) and the mixture was stirred at rt overnight. The reaction mixture was acidified with 2 N HC1 and extracted with EtOAc, washed with brine and dried (MgS04). Evaporation of the solvent afforded Cap-9 as a white solid.XH NMR (400MHz, CHLOROFORM-d) delta 2.21 – 2.01 (m, 5 H), 1.92 – 1.87 (m, J= 6.8, 3.2, 3.2 Hz, 2 H), 1.86 – 1.79 (m, J= 6.7, 3.1 Hz, 2 H).

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; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); 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. 70347-04-5, name is Methyl 4-methoxy-3-methylbenzoate, A new synthetic method of this compound is introduced below., Product Details of 70347-04-5

Reference example 57 Methyl 3-bromomethyl-4-methoxybenzoate To a solution of methyl 3-methyl-4-methoxybenzoate (3.0g, 16.5mmol) which was prepared in Reference example 56 in carbon tertachloride (100ml) were added N-bromosuccinimide (2.9g, 16.5mmol) and benzoyl peroxide (0.10g), and the mixture was refluxed for 6 hours. After being cooled to 0C, the precipitate was filtered, and to the filtrate was added a saturated aqueous sodium thiosulfate solution (1ml). The solution was stirred for 15 minutes and concentrated in vacuo. To the residue was added water and the solution was extracted with chloroform 50 ml*3). The organic layer was concentrated and the precipitated solid was filtered to give the titled compound as a white solid (3.0 g, 11.7 mmol). Yield: 70%. 1H NMR(CDCl3)delta 8.04-7.99(2H, m), 6.91(1H, d, J = 8.6 Hz), 4.55(2H, s), 3.97(3H, s), 3.89(3H, s).

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; Dainippon Sumitomo Pharma Co., Ltd.; AstraZeneca AB; EP1728792; (2006); A1;,
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Synthetic Route of 41841-16-1, 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. 41841-16-1 name is Methyl 2-(4-bromophenyl)acetate, 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.

Preparation of Intermediate methyl 1-(4-bromoDhenyl)cvclobutanecarboxylate (1AH-1); Sodium hydride (3.5g, 88mmol) was stirred as a suspension in dimethylformamide (250ml) under argon. This was warmed to 35C and methyl 2-(4-bromophenyl)acetate (10g, 44mmol) in dimethylformamide (10OmL) was added drop wise over 1 hour and then stirred at 300C for 1 hour. To this the 1 ,3-dibromopropane (4.4ml, 44mmol) in dimtheylformamide (50ml) was added drop wise over 1 hour, and this was left to stir at room temperature overnight. The reaction was incomplete. Sodium hydride (3.5g, 88mmol) was prepared in dimethylformamide (100ml) at 35C and was added to this drop wise to the reaction mixture over 1 hour. This was again left to stir at room temperature overnight. Saturated aqueous ammonium chloride solution (200ml) was carefully added, followed by water (500ml). The product was extracted with ethyl acetate (2 x 500ml), washed with water (3 x 500ml), and brine (2 x 500ml). The organic solution was then dried over magnesium sulfate, filtered, and evaporated. The crude product was purified by flash chromatography (12.5% ethyl acetate in heptane)to methyl 1-(4-bromophenyl)cyclobutanecarboxylate (900mg, 3.3mmol, 7.5%).1 H NMR (400MHz CDCI3) 7.45 (d, 2H), 7.15 (d, 2H), 3.65 (s, 3H), 2.80 (m, 2H), 2.45 (m, 2H), 2.05 (m 1 H), 1.85 (m, 1 H)

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

Reference:
Patent; PFIZER INC.; ASPNES, Gary, Erik; DOW, Robert, Lee; MUNCHHOF, Michael, John; WO2010/86820; (2010); 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 56741-34-5 as follows. name: Methyl 5-amino-2-fluorobenzoate

EXAMPLE 8 Methyl 2-bromo-3-(3-methoxycarbonyl-4-fluorophenyl)propionate To a solution of methyl 5-amino-2-fluorobenzoate (4.12 g) in 47% hydrobromic acid (11.4 ml), methanol (20 ml) and acetone (50 ml), a solution of sodium nitrite (1.88 g) in water (3 ml) was slowly added dropwise under cooling with salt-ice and stirring so as to keep an internal temperature of not higher than -5 C. After stirred for 30 minutes as it was, ice bath was removed, methyl acrylate (13.3 ml) was added, and cuprous oxide (225 mg) was added little by little while stirring vigorously. After no nitrogen became to generate, the reaction liquor was concentrated under reduced pressure. The residue was dissolved into ethyl acetate, washed with water, saturated aqueous solution of sodium hydrogencarbonate and water in order, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by means of silica gel column chromatography (developing solvent; n-hexane:ethyl acetate=10:1) to obtain 3.48 g (45%) of aimed compound as an oily material. 1 H NMR (CDCl3), delta: 3.25 (1H, dd, J=7.3, 14.6 Hz), 3.46 (1H, dd, J=7.8, 14.2 Hz), 3.75 (3H, s), 3.93 (3H, s), 4.38 (1H, t, J=7.8 Hz), 7.09 (1H, dd, J=8.8, 10.8 Hz), 7.38 (1H, ddd, J=2.4, 4.4, 8.8 Hz), 7.80 (1H, dd, J=2.4, 6.3 Hz) MS(m/z): 318, 320 (M+)

According to the analysis of related databases, 56741-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kyorin Pharameuticals Co., Ltd.; US6001862; (1999); 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. 39503-51-0, name is Methyl 5-bromo-2,4-dimethoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Methyl 5-bromo-2,4-dimethoxybenzoate

To potassium isopropylidene trifluoroborate (4.87 g, 32.7 mmol) and 5-bromo-2,4-dimethoxybenzoic acid methyl ester (7.5 g, 27.3 mmol) in THF (195 ml) was added Cs2CO3 (26.6 g, 81.8 mmol) in water (39 ml). The reaction was degassed and Pd(PPh3)4 (1.58 g, 1.36 mmol) added. The reaction was heated at reflux for three days then quenched by adding water and extracted with EtOAc (¡Á2). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated to leave an orange solid. The product was taken up in EtOAc again and the precipitate filtered. The filtrate was evaporated to dryness to yield 5-isopropenyl-2,4-dimethoxy-benzoic acid methyl ester (6.2 g). 1H NMR (Me-d3-OD) 7.68 (1H, s), 6.66 (1H, s), 5.10-5.08 (1H, m), 5.02-5.00 (1H, m), 3.93 (3H, s), 3.92 (3H, s), 3.84 (3H, s), 2.08-2.06 (3H, m). MS: [M+H]+ 237.

The synthetic route of 39503-51-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2010/152184; (2010); A1;,
Ester – Wikipedia,
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