Author: Jessica.F

Some common heterocyclic compound, 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, molecular formula is C9H8ClN3O2, 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: C9H8ClN3O2

To (2R)-2-(3-fluoro-5-(methylthio)phenyl)pyrrolidine _ (Preparation 9, 0.30mmol, 1.2 equiv.), ethyl 6-chloroimidazo[1 ,2-b]pyridazine-3-carboxylate (0.25mmol) and KF (2.8mmol, 11 equiv.) was added DMSO (2ml) and the reaction was heated at 130C. After overnight reaction the reaction mixture was cooled to rt. Water (10ml) and EtOAc (10 ml) were added and the layers partitioned. The organic layer was washed three times with brine (10ml), dried over Na2S04 and the solvent was removed under vacuum. The crude material containing the title compound was used without further purification. LCMS m/z = 401.1 [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 1150566-27-0, its application will become more common.

Reference:
Patent; BENEVOLENTAI BIO LIMITED; BROWN, Alan; GLEN, Angela; (115 pag.)WO2020/39209; (2020); A1;,
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680-65-9, A common compound: 680-65-9, name is Diethyl difluoromalonate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

5 g (1.0 eq., 25.49 mmol) of the compound 37 was dissolved in 40 mL of methanol, and 30 mL of methanol solution of sodium hydroxide (1.43 g (1.0 eq., 25.49 mmol)) was added dropwise thereto. It was then stirred for 3 hours at room temperature. After confirming by TLC the disappearance of the reacting materials, benzyl amine (8.4 mL (3.0 eq., 76.47 mmol)) was added and stirred overnight at 55 C. The reaction solution was concentrated under reduced pressure by using an evaporator, and the precipitated solids were added with diethyl ether followed by washing and filtering. The washed solids were dissolved in 1 M HCl. Then, liquid fractionation extraction was performed 3 times using ethyl acetate. The collected organic layer was washed with a saturated aqueous solution of NaCl. After drying over magnesium sulfate, it was concentrated under reduced pressure by using an evaporator in water bath at 40 C. to obtain the residues (compound 39). It was directly subjected to the following reducing reaction.

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, Diethyl difluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Seikagaku Corporation; Miyamoto, Kenji; Yasuda, Yosuke; Takeuchi, Hisayuki; Yoshioka, Keiji; (69 pag.)US2016/151506; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 58656-98-7, name is tert-Butyl 4-fluorobenzoate, 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 58656-98-7, Application In Synthesis of tert-Butyl 4-fluorobenzoate

Example 57A 4-(4-trans-aminocyclohexyloxy)-benzoic acid tert-butyl ester To a stirred solution of trans-4-aminocyclohexanol (345 mg, 3 mmol) in DMF (9 mL) at 0 C. was added 60% NaH in mineral oil (360 mg, 9 mmol). The reaction mixture was stirred at 0 C. for 1/2 hour and then tert-butyl 4-fluorobenzoate (706 mg, 3.6 mmol) was added. It was heated to 60 C. for 2 hours and stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water (3 times) and brine. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the titled compound. MS (DCI) m/z 292 (M+H)+.

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 4-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Madar, David J.; Djuric, Stevan W.; Michmerhuizen, Melissa J.; Kopecka, Hana A.; Li, Xiaofeng; Longenecker, Kenton L.; Pei, Zhonghua; Pireh, Daisy; Sham, Hing L.; Stewart, Kent D.; Szczepankiewicz, Bruce G.; Wiedeman, Paul E.; Yong, Hong; US2004/259843; (2004); A1;; ; Patent; Madar, David J.; Djuric, Stevan W.; Michmerhuizen, Melissa J.; Kopecka, Hana A.; Li, Xiaofeng; Longenecker, Kenton L.; Pei, Zhonghua; Pireh, Daisy; Sham, Hing L.; Stewart, Kent D.; Szczepankiewicz, Bruce G.; Wiedeman, Paul E.; Yong, Hong; US2005/215784; (2005); 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. 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

A solution of 25g ethyl (4-bromophenyl)acetate in100 ml DMF was added dropwise to 13.8 gpotassium-tert.butylate in 150 ml DMF at 0C and stirred for additional 30 minat 0C. Then 18.4 g bromocyclopentane were added dropwise at 0C and the reactionmixture was stirred until reaction completion. The mixture was given on water,extracted with EE, the combined organic layers washed with water and brine,dried with Na2SO4, filtered and evaporated to dryness.Yield: 35.6 g, used without further purification in the next step.

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:
Article; Koppitz, Marcus; Braeuer, Nico; Ter Laak, Antonius; Irlbacher, Horst; Rotgeri, Andrea; Coelho, Anne-Marie; Walter, Daryl; Steinmeyer, Andreas; Zollner, Thomas M.; Peters, Michaele; Nagel, Jens; Bioorganic and Medicinal Chemistry Letters; vol. 29; 18; (2019); p. 2700 – 2705;,
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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. 15964-79-1, name is Methyl 2-(3,4-dimethoxyphenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C11H14O4

l-(4-Bromophenyl)-4-(3,4-dimethoxyphenyl)butane-l,3-dione; Sodium hydride (60% dispersion, 3.80 g, 95.1 mmol) was added portionwise to methyl 2-(3,4-dimethoxyphenyl)acetate (10 g, 47.6 mmol) in Et2O (100 ml) at O0C. A solution of 4′-bromoacetophenone (9.48 g, 47.6 mmol) in Et2O (50 ml) was added dropwise over 1 h. The mixture was heated at reflux for 16 h, cooled, poured into ice/HCl (2 M), extracted with Et2O (3 x 100 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was crystallized from MeOH to give the title compound (9 g, 50 %) as a tan powder.

The synthetic route of 15964-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ESSILOR INTERNATIONAL (COMPAGNIE GENERALE D’OPTIQUE); WO2008/28930; (2008); 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. 18281-05-5, name is Ethyl icosanoate, A new synthetic method of this compound is introduced below., Computed Properties of C22H44O2

EXAMPLE 111 (+-)-cis,trans-2-[[[[(4-octadecyltetrahydrofuran-2-yl)methoxy]carbonyl]amino]methyl]pyridine Following the procedure described in example 9, but using in place of the compound prepared in example 4b, (+-)-cis,trans-(4-octadecyltetrahydrofuran-2-yl)methanol obtained as in example 70c starting from ethyl eicosanate, the title compound was obtained as a colourless oil and in quantitative yield. Rf: 0.24 (silicagel, hexane:ethyl acetate 1:1); IR (film) v: 3317, 3050, 2913, 2846, 1714, 1588, 1566, 1463, 1211 cm-1; 1 H-NMR (90 MHz, CDCl3) delta: 0.87 (m, 3H), 1.0-2.6 (complex signal, 36 H), 3.40 (m, 1H), 4.08 (m, 4H), 4.50 (d, J=5.4 Hz, 2 H), 5.96 (m, NH), 7.28 (m, 2H), 7.64 (t of d, Ja=7.6 Hz, Jb=1.8 Hz, 1H), 8.51 (d, J=4.6 Hz, 1H).

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; J Uriach & Cia S.A.; US4997843; (1991); A;,
Ester – Wikipedia,
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Synthetic Route of 106896-49-5,Some common heterocyclic compound, 106896-49-5, name is Methyl 4-amino-3-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.

General procedure: A mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 C for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50% EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80%) as a colourless syrup.

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

Reference:
Article; Kurissery, A. Tony; Rajkumar, G. Abraham; Arvapalli, Venkata Satyanarayana; Pitchumani, Venkatachalam; Tetrahedron Letters; vol. 58; 37; (2017); p. 3607 – 3611;,
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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. 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-amino-5-bromo-2-methylbenzoate

The 2-methyl-3-amino-5-bromobenzoic acid methyl ester (1.5g, 6 . 1mmol) dissolved in 15 ml chloroform, by adding potassium acetate (0.63g, 6 . 4mmol) and acetic anhydride (1.26g, 12 . 3mmol), stirring the mixture at room temperature for 12 hours. Then added tert-butyl nitrite (2.53g, 24 . 6mmol) and 18-crown -6 (0.57g, 2 . 15mmol), 65 C lower stirring 3 hours. After finishing the reaction, cooling to room temperature, add saturated sodium bicarbonate aqueous solution and dichloromethane, separating, sodium sulfate drying, extraction, concentration to obtain the product.

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; Sichuan Univeristy; Yu, Luoting; Wei, Yuquan; (54 pag.)CN105037360; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35418-07-6, name is Methyl 3-(4-aminophenyl)propanoate, 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 35418-07-6, Computed Properties of C10H13NO2

General procedure: To a solution of 3a (1 g) in ethanol was added Pd/C (5%, 0.1 g) and the mixture was stirred for 24 hrs at room temperature in a hydrogen atmosphere under atmospheric pressure. Insoluble matters were removed using Celite, and the filtrate was concentrated in vacuo to give the desired product 4a (0.76 g) as a yellow solid. To a solution of carboxylic acid (1 equiv) in CH2Cl2 (15 mL) at 0 C was added DMAP (1 equiv) and EDCI (1 equiv). The reaction mixture was stirred at 0 C for 45 minutes. At this time 4a (1 equiv) was added and the mixture was warmed to room temperature and stirred overnight. The resulting mixture was concentrated in vacuo, partitioned between 1.0 M HCl (20 ml) and ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2 × 15 ml), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 5, v/v) as eluent to afford the product as a white solid. To a solution of the obtained solid (1 equiv) in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 2-17 as white solid.

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, Methyl 3-(4-aminophenyl)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yang, Jianyong; Li, Zheng; Li, Huilan; Liu, Chunxia; Wang, Nasi; Shi, Wei; Liao, Chen; Cai, Xingguang; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 25; 8; (2017); p. 2445 – 2450;,
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Application of 148547-19-7, 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. 148547-19-7 name is Methyl 4-bromo-3-methylbenzoate, 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.

Step A. (2-Methyl-2′-methoxy-[1,1′-biphenyl]-4-yl)carboxylic acid methyl ester A mixture of 3-methyl-4-bromobenzoic acid methyl ester (2.0 g, 8.7 mmol), 2-methoxyphenyl boronic acid (1.32 g, 8.7 mmol) and sodium carbonate (4.1 g, 38.7 mmol) in toluene:ethanol:water (50 mL:25 mL: 25 mL) was purged with nitrogen for 1 hour. After addition of the tetrakis(triphenylphosphine) palladium(0) catalyst (0.50 g, 0.43 mmol), the reaction mixture was heated at 100 C. overnight. After cooling, the reaction was filtered through Celite and the cake washed with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a brown oil. Purification by flash chromatography on silica gel with a solvent gradient from 20% to 50% dichloromethane in hexane gave 2.0 g of product as a colorless oil. 1H NMR (DMSO-d6, 400 MHz): delta2.09 (s, 3H), 3.70 (s, 3H), 3.85 (s, 3H), 7.00-7.04 (m, 1H), 7.08-7.11 (m, 2H), 7.23 (d, 1H), 7.37-7.41 (m, 1H), 7.77-7.79 (m, 1H), 7.83-7.84 (m, 1H). MS [(+)APCI, m/z]: 257[M+H]+. Anal. Calcd. for C16H16O3: C, 74.98, H, 6.29. Found: C, 74.06, H, 6.17.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-bromo-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Wyeth; US2003/8863; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics