Tag: M.W=200-300

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. 1186-73-8, name is Trimethyl methanetricarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 1186-73-8

A mixture of N-benzyl-2-chloro-6-isopropyl-3-(3-methoxypropoxy)-6,7-dihydroquinolin-8(5H)-imine (0.34 g, 0.85 mmol) and trimethyl methanetricarboxylate (0.491 g, 2.50 mmol) in diglyme (3 mL) was heated at 180 C in a microwave reactor for 45 min. The reaction mixture was concentrated under reduced pressure and the residue purified by normal phase SiCb chromatography (0-70 % EtO Ac/hexanes) to give methyl 1-benzyl-9-chloro-4-hydroxy-5-isopropyl-8-(3-methoxypropoxy)-2-oxo-1,2,5,6-tetrahydro-1,10-phenanthroline-3-carboxylate as a yellow oil (0.12 g, 27 %, m/z: 527 [M+H] observed). NMR (300 MHz, CDCl3): d 13.80 (s, 1H), 7.28 (s, 1H), 7.16-6.98 (m, 5H), 6.30-6.10 (m, 2H), 4.20-4.11 (m, 2H), 4.02 (s, 3H), 3.59 (t, J= 6.0 Hz, 2H), 3.37 (s, 3H), 3.01-2.96 (m, 1H), 2.89-2.75 (m,2H), 2.16-2.08 (m, 2H), 1.42-1.37 (m, 1H), 0.84 (d, J= 6.0 Hz, 3H), 0.78 (d, J= 6.0 Hz, 3H).

The synthetic route of 1186-73-8 has been constantly updated, and we look forward to future research findings.

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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24807-40-7, 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. 24807-40-7, name is Methyl 3-(4-(benzyloxy)phenyl)propanoate, This compound has unique chemical properties. The synthetic route is as follows.

Methyl 2-((4-((phenylmethyl)oxy)phenyI)methyl)-4-pentenoate(33.1); To a solution of lithium diisopropylamide (6.5 mL, 13.0 mmol, 2.0M in heptanelambdaTHF/ethylbenzene) in THF (25.0 mL) and l,3-dimethyl-3,4,5,6- tetrahydro-2(lH)-pyrimidinone (5.0 mL) was slowly added methyl 3-(4- (benzyloxy)phenyl)propanoate 23.1 (3.00 g, 1 1 mmol) in THF (10 mL) and 1 ,3- dimethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidinone (2.5 mL) at -780C. The resulting mixture was stirred at -780C for 30 minutes and then allyl iodide (1.08 mL, 13.0 mmol) in THF (5.0 mL) was added. The reaction mixture was stirred at the same temperature for 20 minutes. The reaction was then stirred at room temperature for 16 hours. The reaction was quenched with water (30.0 mL). The solvent was concentrated in vacuo, and the residue was disolved in EtOAc (100 mL) and washed with brine (2 x 25 mL) and then dried with Na2SO4. The product thus obtained was purified on a silica gel column, to give the title compound 33.1. 1H NMR (500 MHz, CDCl3) delta ppm 2.29 – 2.34 (m, 1 H) 2.39 – 2.44 (m, 1 H) 2.63 – 2.79 (m, 2 H) 2.91- 2.96 (m, 1 H) 3.64 (s, 3 H) 5.06 – 5.18 (m, 4 H) 5.67 – 5.85 (m, 1 H) 6.88 – 7.03 (m, 2 H) 7.03 – 7.18 (m, 2 H) 7.34 – 7.49 (m, 5 H).

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; AMGEN INC.; WO2008/130514; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, molecular formula is C9H9BrO2, 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. 99548-54-6

< Step 2>; Methyl 3-bromo-2-methylbenzoate (4.67 g, 20 mmol) obtained in Step 1 and 100 mi of benzene were placed into a flask, and N-bromosuccinimide (4.37 g, 25 mmol) and 2,2′-azobisisobutylnitrile (0.336 g, 2 mmol) were added thereto. The resulting mixture was refluxed for 6 hours, cooled to 0 C , and filtered to remove precipitate. The resulting solution was washed successively with 10% sodium sulfite and saturated sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was removed under a reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain methyl 3- bromo-2-(bromomethyl)benzoate (5.27 g (84%)).1H nuMR (300 MHz, CDCl3) delta 7.62 (d, IH, J = 7.9 Hz), 7.49 (dd, IH, J = 7.9, 0.9 Hz), 6.99 (t, IH, J= 7.9 Hz), 4.88 (s, 2H), 3.70 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis Methyl 3-bromo-2-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2009/51417; (2009); A2;,
Ester – Wikipedia,
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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. 115118-68-8 name is Diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate, 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. 115118-68-8

3-Oxo-cyclobutanecarboxylic acid; [1244] 3,3-Dimethoxy-cyclobutane-1,1-dicarboxylic acid diisopropyl ester (0.1 mmol, 30 g) was refluxed in 20% HCI aqueous solution for 60 h. Part of the HCI aqueous solution was evaporated under high vacuum and light brown color oil remained. The oil was dissolved by EtOAc and washed by brine. The organic layer was dried by NaS04, filtered, and evaporated under vacuum. The title compound was obtained as an off-white solid after recrystallization from chloroform.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2005/97800; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 55666-43-8, name is tert-Butyl 3-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 55666-43-8, 55666-43-8

Preparation in accordance with scheme 6. To a solution of 6-((2,6- dichlorobenzyl)oxy) -1,2,3, 4-tetrahydro-2, 7 -naphthyridine (80 mg; 0.259 mmol; 1 eq) in 10 mL acetonitrile were added tert-butyl 3-bromopropanoate (56.8 mg; 0.272 mmol; 1.05 eq) and triethylamine (131 mg; 1.29 mmol; 5 eq). The mixture wasstirred at RT overnight. The mixture was extracted with water/ethylacetate. The organic phase was washed with water, dried with MgSO4, and evaporated. The residue was purified by flash chromatography (4g silica gel; 3-10% MeOH in DCM) giving the product with a yield of 40 mg (0.09 1 mmol; 35.3%).

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, tert-Butyl 3-bromopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; ABBVIE DEUTSCHLAND GMBH & CO. KG; LANGE, Udo; OCHSE, Michael; VAN DER KAM, Elizabeth; VAN BERGEIJK, Jeroen; TURNER, Sean; OELLIEN, Frank; WALLESER, Patrick; AMBERG, Wilhelm; HORNBERGER, Wilfried; GENESTE, Herve; MEZLER, Mario; HUTCHINS, Charles; (301 pag.)WO2017/36978; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

214262-88-1, Adding a certain compound to certain chemical reactions, such as: 214262-88-1, name is Methyl 2-(2-chloro-4-fluorophenyl)acetate, 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 214262-88-1.

Example 25. 2-(2-chloro-4-fluorophenyl)- 6-methoxy -8-(6-methyl-7-oxo-6,7-dihydro- -pyrrolo[2,3-c]pyridin-4-yl)-2H-l,4-benzoxazin-3(4H)-one A solution of methyl (2-chloro-4-fluorophenyl)acetate (100 mg, 0.5 mmol) (Acros Organics cat 30478) and N-bromosuccinimide (90 mg, 0.5 mmol) in carbon tetrachloride (0.7 mL) was heated to 100 C for 1 h. The reaction mixture was cooled to room temperature, filtered, and partitioned between ethyl acetate and water. The combined organic layers were washed with brine, dried over MgSC , filtered, and concentrated to afford crude methyl bromo(2-chloro-4-fluorophenyl)acetate as light yellow semi solid (120 mg, 90%).

According to the analysis of related databases, 214262-88-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; COMBS, Andrew, P.; MADUSKUIE, Thomas, P., Jr.; FALAHATPISHEH, Nikoo; WO2015/164480; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 2178-24-7, name is Ethyl (2-bromophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 2178-24-7

b) 4-(alpha-Ethoxycarbonyl-benzyloxy)benzyl alcohol 41.8 g (0.172 mol) of ethyl 2-bromo-phenylacetate and 21.3 g (0.172 mol) of 4-hydroxybenzyl alcohol are dissolved in 850 ml of acetone and 24.8 g (0.18 mol) of potassium carbonate and 5.0 g (0.03 mol) of potassium iodide are added thereto. The reaction mixture is refluxed for 60 hours with stirring. Then the inorganic salts are filtered off and the residue is washed with hot acetone. The filtrate is evaporated down and the residue is purified over a silica gel column (particle size: 0.063-0.02 mm), initially using petroleum ether as eluant and then using mixtures of petroleum ether and ethyl acetate of increasing polarity (9:1, 8:2 and 7:3). The unified fractions are evaporated down in vacuo. Yield: 30.65 g (62.5% of theory), Rf value: 0.40 (silica gel; eluant: ethyl acetate/petroleum ether=3:7)

The synthetic route of 2178-24-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dr. Karl Thomae GmbH; US5519138; (1996); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 24398-88-7, name is Ethyl 3-bromobenzoate, 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 24398-88-7, 24398-88-7

Preparation of ethyl-3-isopropylthiobenzoate [formula 6] A solution of palladium acetate (4.5 mg, 0.02 mmol) and Xantphos (12.7 mg, 0.022 mmol) in DMF (1 mL) was stirred for 5 minutes under a nitrogen atmosphere. To this solution was added ethyl 3-bromobenzoate (1 14.5 mg, 0.5 mmol) dissolved in 0.5 mL of DMF and then the reaction mixture was stirred for 10 minutes at room temperature. In(SPr’)3 (57 mg, 0.168 mmol) in DMF ( 1 mL) and diisopropylethyl amine (65 mg, 0.5 mmol) were added to this reaction mixture. The reaction mixture was stirred for 2 hours at 100 degrees Celsius. The solution was cooled to room temperature and then 1 mL of hydrochloric acid (5 % of aqueous solution) was added to stop the reaction. The crude product was extracted with diethyl ether (15 mL, 3 times) and sequentially washed with 10 mL of water, a saturated NaHCO3 (10 mL) solution and a saturated NaCl (20 mL) solution. The extracted organic compound was dried over anhydrous MgSO4 and then filtered. After evaporation of solvents, the crude product was purified by column chromatography to give ethyl-3-isopropylthio benzoate (102 mg, 91 %) (formula 6).1H-NMR (400 MHz, CDCl3, 25 degrees Celsius) delta 8.06(s, IH), 7.89(d, J=7.8Hz, IH), 7.56(d, J=7.8Hz, IH), 7.36(t, J=7.8Hz, IH), 4.38(q, J=7.1Hz, 2H), 3.44(sep, J=6.7Hz, IH), 1.40(t, J =7. IHz, 3H), 1.31(d, J =6.7Hz, 6H).

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, Ethyl 3-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KNU-INDUSTRY COOPERATION FOUNDATION; WO2009/69888; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

154825-97-5, 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. 154825-97-5, name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, A new synthetic method of this compound is introduced below.

Example 72C; methyl 2-{4-[(7-amino-5-methyl[l,2,4]triazolo[l,5-alpha]pyrimidin-6-yl)ethynyl]phenyl}-2- methylpropanoate A mixture of Example 72B (17 mg, 0.1 mmol), methyl 2-(4-bromophenyl)-2- methylpropanoate (38 mg, 0.15 mmol), bis(triphenylphosphine)palladium(II) dichloride (3.5 mg, 0.005 mmol), CuI (1 mg, 0.005 mmol), and triethylamine (28 muL, 0.2 mmol) in acetonitrile (500 muL) was heated at 95 0C under nitrogen for 1 h. The resulting mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated in vacuuo. The residue was purified by flash chromatograph on silica gel (eluting with ethyl acetate) to provide the title compound as a white solid (16 mg, 45% yield). 1H NMR (300 MHz, DMSO-J6) delta 8.44 (s, 3 H), 7.64 (d, J = 8.48 Hz, 2 H), 7.36 (d, J= 8.48 Hz, 2 H), 3.61 (s, 3 H), 2.60 (s, 3 H), 1.52 (s, 6 H). MS (ESI) m/z 350 (M+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; ABBOTT LABORATORIES; WO2008/134690; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 6279-86-3, name is Triethyl methanetricarboxylate, This compound has unique chemical properties. The synthetic route is as follows., 6279-86-3

Synthesis of sodium salt of 2-ethoxycarbonyl-malonic acid diethyl ester; Sodium ethoxide solution was prepared in a flame-dried 100 mL flask under a flow of argon gas using sodium metal (0.21 g, 9.14 mmol) and dry ethanol and was added slowly to a solution of triethyl methanetricarboxylate (2.12 g, 9.14 mmol) in 20 mL of THF while the reaction temperature was maintained around 1 0C using an ice bath. This resulted in the precipitation of product as white solid. The solvent was removed under reduced pressure and the salt was washed with dry petroleum ether and dried under high vacuum to get the product, which was non-hygroscopic in nature. 1H NMR (300 MHz, D2O): 1.22 (t, 9H), 4.08 (q, 6H). Mass: 232 [(MM)-Na+].

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; INDIAN INSTITUTE OF TECHNOLOGY BOMBAY; WO2006/117800; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics