Tag: M.W=100-200

Synthetic Route of 685-88-1,Some common heterocyclic compound, 685-88-1, name is Diethyl fluoromalonate, molecular formula is C7H11FO4, 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.

6-Fluoroimidazo[1 ,2-a]pyridine-3-carboximidamide (Preparation 1 b, 2.0 g, 8.39 mmol,) was added portionwise to a stirred solution of sodium (0.46 g, 20.21 mmol) in methanol (35 mL) at 0 C. Diethyl 2-fluoromalonate (2.65 mL, 16.8 mmol) was then added and the reaction mixture was stirred from 0 C to room temperature overnight. The solvent was evaporated to dryness and the resulting crude was dissolved in water (90 mL). After stirring for 30 min, a 2N solution of hydrochloric acid was added until acid pH. The solid formed was filtered and dried to yield the title compound (0.95 g, 43%) as a brown solid that was used in the next synthetic step without further purification. LRMS (m/z): 265 (M+1 )+ 1H NMR delta (300 MHz, DMSO-d6): 7.6 (s, 1 H), 7.8 (s, 1 H), 8.7 (s, 1 H), 10.1 (s, 1 H), 12.6 (bs, 1 H).

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

Reference:
Patent; ALMIRALL, S.A.; BACH TANA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/91531; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 89-91-8, name is Methyl 2,2-dimethoxyacetate, 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 89-91-8, name: Methyl 2,2-dimethoxyacetate

Compound 7 (15mmol) and methyl 2,2-dimethoxypropionate (30mmol) were kept in a 10mL screw-capped vial was stirred at 80C overnight. The reaction mixture was loaded on silica and resulting 110 dimethoxy acetamide intermediate 8 was purified by silica column chromatography using hexane and ethylacetate at a ratio of 2:1. The resulted compound without further purification was dissolved in 5mL concentrated sulfuric acid and stirred at 40C overnight. Subsequently, the acidic solution poured into ice-water, and the precipitate was collected and washed with water and diluted sodium bicarbonate solution [16]. The yield was 42%.1H NMR (500MHz, DMSO-d6) delta 8.91 (s, 1H, H1-isoquinoline), 7.64 (d, J=8.4Hz, 1H), 7.49 (d, J=8.4Hz, 1H), 6.87 (s, 1H, H4-isoquinoline), 5.74 (bs, 1H, OH), 2.54 (s, 3H, CH3).

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

Reference:
Article; Assadieskandar, Amir; Yu, Caiqun; Maisonneuve, Pierre; Liu, Xu; Chen, Ying-Chu; Prakash, G.K. Surya; Kurinov, Igor; Sicheri, Frank; Zhang, Chao; European Journal of Medicinal Chemistry; vol. 146; (2018); p. 519 – 528;,
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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. 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 3-chlorocyclobutanecarboxylate

Step 1: To a 3-neck flask that had been purged and maintained with an inert atmosphere of nitrogen, was placed a solution of phenol (111 g, 1.18 mol) in DMSO (2000 mL). To thissolution was added potassium tert-butoxide (240 g, 2.14 mol), and the mixture was heated to80C with vigorous stirring under an argon atmosphere for 15 minutes. To the above solution was added methyl 3-chlorocyclobutanecarboxylate (160 g, 1.08 mol) dropwise with stirring followed by tetrabutylammonium iodide (238 g, 0.646 mol). The reaction mixture was stirred for 1.5 h at 80C. The mixture was cooled to 10C, quenched with water (30 mL), and theaqueous layer was extracted with EtOAc (3 x 1000 mL). The combined organic layers were washed with brine (200 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (1:40 EtOAc:petroleum ether) to afford methyl 3-phenoxycyclobutanecarboxylate as a 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; MERCK SHARP & DOHME CORP.; FISCHER, Christian; BOGEN, Stephane, L.; CHILDERS, Matthew, L.; LLINAS, Francesc Xavier Fradera; ELLIS, J. Michael; ESPOSITE, Sara; HONG, Qingmei; HUANG, Chunhui; KIM, Alexander, J.; LAMPE, John, W.; MACHACEK, Michelle, R.; MCMASTERS, Daniel, R.; OTTE, Ryan, D.; PARKER, Dann, L., Jr.; REUTERSHAN, Michael; SCIAMMETTA, Nunzio; SHAO, Pengcheng, P.; SLOMAN, David, L.; UJJAINWALLA, Feroze; WHITE, Catherine; WU, Zhicai; YU, Yang; ZHAO, Kake; GIBEAU, Craig; BIFTU, Tesfaye; BIJU, Purakkattle; CHEN, Lei; CLOSE, Joshua; FULLER, Peter, H.; HUANG, Xianhai; PARK, Min, K.; SIMOV, Vladimir; WITTER, David, J.; ZHANG, Hongjun; (297 pag.)WO2016/89797; (2016); A1;,
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Related Products of 23680-40-2, The chemical industry reduces the impact on the environment during synthesis 23680-40-2, name is Methyl 3-bromopropiolate, I believe this compound will play a more active role in future production and life.

General procedure: Methyl 3-bromopropiolate 2 (0.5 mmol), furan 1 (0.6 mmol) and distilled toluene (1.5 mL) were added to atwo-necked flask, and the mixture was stirred at reflux for 24 h under nitrogen atmosphere. After completion ofthe initial DielsAlder reaction, silica gel (150 mg) was added under flow of nitrogen and the mixture wasstirred at reflux for 2 h. After removal of the solvent and filtration, a product 4 was purified by silica gelcolumn chromatography or PTLC using a mixture of ethyl acetate and n-hexane as an eluent.

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

Reference:
Article; Shinohara, Hiroyuki; Sonoda, Motohiro; Hayagane, Naoya; Kita, Shota; Tanimori, Shinji; Ogawa, Akiya; Tetrahedron Letters; vol. 55; 38; (2014); p. 5302 – 5305;,
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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. 454-31-9, name is Ethyl 2,2-difluoroacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Ethyl 2,2-difluoroacetate

0 g of (1R,2S)-2-amino-1-(4-chlorophenyl)-3-fluoropropan-1-ol was dissolved in 350ml_ methanol, and then 5g of triethyl amine and 30.5g of ethyl difluoroacetate were added and stirred for 12 hours at room temperature. The solvent was evaporated off under reduced pressure, and the residue was recrystallized in isopropanol and water to obtain 12.7g of a white solid (yield 92%).

The synthetic route of 454-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZOETIS SERVICES LLC.; DEJONG, Randall Lee; KARRICK, Gregory Lee; STUK, Timothy Lee; (56 pag.)WO2020/68607; (2020); A1;,
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3196-15-4, name is Methyl 2-bromobutyrate, 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. Product Details of 3196-15-4

General procedure: As part of this general procedure, the appropriate diphenyl diselenide (9.5 mmol) dissolved in a 1:1 mixture of water and THF (50 mL) underprotective nitrogen gas, sodiumborohydride (47.5 mmol) was added and the mixture was stirred for around 35 minutes while observing adecolorization in the first 1-3 minutes. Next, a solution of a methyl -2-bromo-acetate derivatives (19.37 mmol) in THF or DCM (5 mL) wasadded and the reaction was stirred at room temperature and monitored via thin layer chromatography (TLC). Upon consumption of the startingmaterial usually occuring after 24-48 hours, the reaction mixture was diluted with 50 mL of a saturated aqueous solution of ammoniumchloride and extracted with diethyl ether. The combined organic extracts dried over sodium sulfate, and the solvent was evaporated under reducedpressure to obtain the desired intermediate, which was used without further purification.

The synthetic route of 3196-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ali, Wesam; Battistelli, Cecilia; D?browska, Monika; Handzlik, Jadwiga; Honkisz-Orzechowska, Ewelina; Jacob, Claus; Kincses, Annamaria; Latacz, Gniewomir; Nove, Marta; Rasile, Manuela Monica; Romanelli, Annalisa; Spengler, Gabriella; Starek, Ma?gorzata; Szyma?ska, Ewa; Zwergel, Clemens; European Journal of Medicinal Chemistry; vol. 200; (2020);,
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Synthetic Route of 369-26-6, These common heterocyclic compound, 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, 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.

HATU (116 mg, 0.305 mmol) was added to picolinic acid (37.5 mg, 0.305 mmol) and DIPEA (66 mu, 0.381 mmol) in DMF (2 ml). After 15 min, methyl 3-amino-4-fluorobenzoate (43 mg, 0.254 mmol) in DMF (1 ml) was added. The mixture was stirred at ambient temperature for 10 d before solvent was evaporated and residue dissolved in EtOAc. The solution was washed with sat. NaHC03, dried (MgS04) and evaporated. Half of the crude material from above (0.127 mmol) was dissolved in dioxane (1.5 ml) and MeCN (1.5 ml). Potassium carbonate (35 mg, 0.254 mmol) was added and the mixture was heated at 180 ¡ãC for 2 h in a microwave reactor. Silica gel was added and solvents evaporated. The dry silica was applied on a flash column which was eluted with 35-50percent) EtOAc in hexanes. Yield: 6 mg (18percent>); colourless oil.

Statistics shows that Methyl 3-amino-4-fluorobenzoate is playing an increasingly important role. we look forward to future research findings about 369-26-6.

Reference:
Patent; KANCERA AB; HAMMER, Kristin; JOeNSSON, Mattias; KRUeGER, Lars; (230 pag.)WO2017/108282; (2017); A1;,
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Application of 927-68-4, The chemical industry reduces the impact on the environment during synthesis 927-68-4, name is 2-Bromoethyl acetate, I believe this compound will play a more active role in future production and life.

Step 14b. 2-(6-Amino-8-(6-iodobenzo[d][1,3]dioxol-5-ylthio)-9H-purin-9-yl)ethyl acetate (Compound 401-38); A mixture of compound 105-38 (3.89 g, 9.41 mmol), Cs2CO3 (3.68 g, 11.3 mmol), 2-bromoethyl acetate (1.89 g, 11.3 mmol) and anhydrous DMF (50 mL) was stirred for 2 h at 50 C. The solvent was removed under high vacuum and the crude purified by column chromatography on silica gel (CH2Cl2/MeOH=60/1) to provide target compound 401-38 as a pale yellow solid (2.95 g, 62.8%): LCMS: 500 [M+1]+.

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, 2-Bromoethyl acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Qian, Changgeng; Cai, Xiong; Gould, Stephen; Zhai, Haixiao; US2008/234297; (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. 13380-85-3, name is Methyl 4-(hydroxymethyl)cyclohexanecarboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H16O3

The compound represented by Formula (1-1-2), pyridine, anddichloromethane were put into a reaction container under a nitrogen atmosphere. With ice cooling, methanesulfonyl chloride wasdropped, followed by stirring at room temperature. After ordinary post-treatment was performed, purification was performed by column chromatography (silica gel) to obtain a compound represented by Formula (1-1-3).

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; DIC CORPORATION; TENG, Yan; HORIGUCHI, Masahiro; KADOMOTO, Yutaka; KOISO, Akihiro; HAYASHI, Masanao; SAITOU, Yoshitaka; LI, Zhimin; (201 pag.)WO2017/79867; (2017); A1;,
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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. 711-01-3, name is Methyl adamantane-1-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Methyl adamantane-1-carboxylate

To 97 g (499 mmol) of methyl 1-adamantanecarboxylate obtained in Preparation Example 1, 485 g of toluene was added, and nitrogen substitution was carried out, followed by cooling with a refrigerant.While maintaining the toluene solution at 10 ¡ã C. or less, 270 mL (540 mmol) of a solution of methylmagnesium chloride in tetrahydrofuran (THF) (2 M) is added dropwiseThereafter, the temperature was raised naturally, and reaction was performed at room temperature (25 ¡ã C.) for 3 hours.The reaction solution was cooled again with a refrigerant, and 179 g (1160 mmol) of methacrylic anhydride was added dropwise while maintaining the temperature at 10 ¡ã C. or less.Thereafter, the temperature was raised naturally, and reaction was performed at room temperature (25 ¡ã C.) for 3 hours.The crude reaction solution was washed with a 2N aqueous hydrochloric acid solution while keeping the temperature at 25 ¡ã C. or lower, and the aqueous layer was separated.Subsequently, the organic layer obtained is washed with a 10percent aqueous sodium hydroxide solution and saturated brine, and the solvent is evaporated under reduced pressure,Crude 1- (1-adamantyl) -1-methylethyl methacrylate was obtained.(Yield 129.9 g, GC purity 82.3percent)

The synthetic route of 711-01-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Osaka Organic Chemical Industry Ltd.; Kojima, Akio; Kono, Naoya; Uenoyama, Yoshitaka; (20 pag.)JP6478447; (2019); B2;,
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