Category: esters-buliding-blocks

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. 4934-99-0, name is Methyl 3-hydroxycyclobutanecarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 4934-99-0

A solution of [1-[6-oxo-5-(trifluoromethyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1,6-dihydropyridazin-4-yl]pyrrolidin-3-yl]methyl 4-methylbenzene-1-sulfonate (1.09 g, 1.99 mmol, 1.00 equiv), methyl 3-hydroxycyclobutane-1-carboxylate (390 mg, 3.00 mmol, 1.50 equiv), sodium hydride (160 mg, 6.67 mmol, 2.00 equiv) in DMF (10 mL) was stirred for 6 h at 80 C. The resulting solution was quenched with 60 ml H2O, then the solution was extracted with EtOAc (3*60 mL) and the organic layers combined. The solution was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column eluting with EtOAc/petroleum ether (1:2) to afford 200 mg (20%) of the title compound as a white solid. LCMS (ESI, m/z): 506.23 [M+H]+

The synthetic route of 4934-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ribon Therapeutics Inc.; Vasbinder, Melissa Marie; Schenkel, Laurie B.; Swinger, Kerren Kalai; Kuntz, Kevin Wayne; (410 pag.)US2019/330194; (2019); A1;,
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Application of 10602-03-6,Some common heterocyclic compound, 10602-03-6, name is Ethyl 4-ethynylbenzoate, molecular formula is C11H10O2, 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 10S1 (0.10 g, 0.59 mmol), Pd(PPh3)4 (41 mg, 0.035 mmol), and CuI (34 mg,0.18 mmol) in degassed tetrahydrofuran/diisopropylamine (THF/DIPA) (5/1, v/v) (19 mL) was added2,5-diiodothiophene (DIT) (0.20 g, 0.59 mmol). The solution was stirred at 60 C for 5 h. After coolingto room temperature, the reaction mixture was diluted with dichloromethane and passed through Celiteto remove the metal catalyst. The solution was washed with 1 N HCl aqueous solution and water, andthen dried over Na2SO4. After removing the solvent by evaporation, the crude product was purified bysilica gel chromatography using hexane-dichloromethane (3/2, v/v) as the eluent to give the desiredproduct as a pale yellow solid (62 mg, 27% yield).

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

Reference:
Article; Ikai, Tomoyuki; Shimizu, Sho; Kudo, Tomoya; Maeda, Katsuhiro; Kanoh, Shigeyoshi; Bulletin of the Chemical Society of Japan; vol. 90; 8; (2017); p. 910 – 918;,
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Adding a certain compound to certain chemical reactions, such as: 344-14-9, name is Dimethyl 2-fluoromalonate, 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 344-14-9, Recommanded Product: 344-14-9

To a solution of methyl carbamimidothioate-^SC^)^ salt (45.90 g, 0.33 mol) and dimethyl 2-fluoromalonate (45.03 g, 0.30 mol) in MeOH (450 mL) at 0C was slowly added sodium methoxide (4.37 M in MeOH, 226 mL, 0.99 mol). The mixture was stirred for 16 hours at room temperature. The solution was concentrated under reduced pressure. The resulting slurry was diluted with water (50 mL) and acidified to about pH 2 by using a 6N HC1 solution. The resulting precipitate was collected, washed with water and dried under vacuum to give 5-fluoro-2-(methylthio)pyrimidine-4,6-diol (46.85 g, 88%).

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, Dimethyl 2-fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PTC THERAPEUTICS, INC.; LEE, Chang-Sun; BAIAZITOV, Ramil; CAO, Liangxian; DAVIS, Thomas, W.; DU, Wu; LIU, Ronggang; MOON, Young-choon; PAGET, Steven, D.; REN, Hongyu; SYDORENKO, Nadiya; WILDE, Richard, Gerald; WO2014/81906; (2014); A2;,
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Adding a certain compound to certain chemical reactions, such as: 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, 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 18469-52-8, COA of Formula: C9H11NO2

General procedure: To a solution of III (1 equiv., 0.10 g) in N-methyl-2-pyrrolidone(10 equiv., 0.3 mL) was added corresponding amine (1.2 equiv.) followedby diisopropylethylamine (3 equiv., 0.2 mL) and the reactionmixture was heated at 130 C for 2 h. The reaction mixture wasthen diluted with water and extracted with ethyl acetate. Ethylacetate layer was dried over anhydrous sodium sulphate and concentratedunder vacuum. The crude products so obtained werepurified by preparative TLC using varying proportions of methanolin dichloromethane as the solvent systems to give the desiredproducts compounds 4-8a and 9a in moderate to good yields.

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:
Article; Koul, Summon; Ramdas, Vidya; Barawkar, Dinesh A.; Waman, Yogesh B.; Prasad, Neela; Madadi, Santosh Kumar; Shejul, Yogesh D.; Bonagiri, Rajesh; Basu, Sujay; Menon, Suraj; Reddy, Srinivasa B.; Chaturvedi, Sandhya; Chennamaneni, Srinivas Rao; Bedse, Gaurav; Thakare, Rhishikesh; Gundu, Jayasagar; Chaudhary, Sumit; De, Siddhartha; Meru, Ashwinkumar V.; Palle, Venkata; Chugh, Anita; Mookhtiar, Kasim A.; Bioorganic and Medicinal Chemistry; vol. 25; 6; (2017); p. 1963 – 1975;,
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Electric Literature of 150529-73-0, 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. 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows.

Tributyltin methoxide (28.3 mL, 98 mmol), the product of preparation 17 (15.0 g, 65mol), isopropenyl acetate (10.8 mL, 98 mmol), palladium (ll) acetate (750 mg, 3.30 mmol) and tri-ortho-tolylphosphine (2.0 g, 6.5 mmol) were stirred together in toluene (75 mL) at 100 C for 5 hours. After cooling, the reaction was diluted with ethyl acetate (150 mL) and 4M aqueous potassium fluoride solution (90 mL), and stirred for 15 minutes. The mixture was filtered through Arbocele and the organic phase was separated and concentrated in vacuo. The residue was then purified by column chromatography on silica gel eluting with diethyl ether : pentane, 0: 100 to 25: 75, followed by dichloromethane to give the title compound as a pale yellow oil in 94% yield (12.6 g). H NMR (400MHz, CDCI3) : 8 : 2. 15 (3H, s), 3.61 (2H, s), 3.69 (5H, s), 7.10-7. 13 (2H, m), 7.19 (1H, d), 7.30 (1H, t); LRMS ESI : m/z 229 [M+Na] +

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

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/92840; (2005); 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. 179688-27-8, name is Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate

In a 10-mL volume stainless steel pressure-resistant vessel were placed 1.02 g (3.3 mmol) of ethyl 4,5-bis(2-methoxyethoxy)anthranilate, 0.96 g (9.1 mmol) of methyl orthoformate, 0.69 g (9.1 mmol) of ammonium acetate, and 5.0 mL of methanol. The reaction was carried out at 110C for 6 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and concentrated under reduced pressure. Then, the concentrate was recrystallized from 20 mL of methanol. The crystalline product was collected by filtration and dried under reduced pressure to give 0.87 g (isolated yield: 91%) of 6,7-bis(2-methoxyethoxy)quinazolin-4-one as a white crystalline product.

The synthetic route of 179688-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ube Industries, Ltd.; EP1477481; (2004); A1;,
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Reference of 18469-52-8, These common heterocyclic compound, 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, 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.

General procedure: To DMF (50 mL) were added methyl 4-(aminomethyl)benzoate (0.015 mol) and K2CO3 (0.025 mol) [45]. The compounds 4a-4j (0.01 mol) in DMF (15 mL) were added dropwise at 0 C over a period of 0.5 h to the stirred reaction mixture, and the reaction was allowed to stir at 40 C for 8 h, then poured slowly into ice water (200 mL) while stirring constantly, and extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with brine (2×50 mL) and dried with Na2SO4. Ethyl acetate was evaporated under reduced pressure to yield the crude products, which were chromatographed on silica gel using ethyl acetate/petroleum ether as an eluent to afford the products 5a-5j.

The synthetic route of 18469-52-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cai, Jin; Wei, Hongtao; Hong, Kwon Ho; Wu, Xiaoqing; Cao, Meng; Zong, Xi; Li, Lushen; Sun, Chunlong; Chen, Junqing; Ji, Min; European Journal of Medicinal Chemistry; vol. 96; (2015); p. 1 – 13;,
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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. 6290-49-9, name is Methyl 2-methoxyacetate, A new synthetic method of this compound is introduced below., Product Details of 6290-49-9

Intermediate 30 l-(3,5-Difluoropyridin-2-yl)-2-methoxyethanone3,5-Difluoropyridine (5.0 g, 43.45 mmol) in THF was cooled to -720C (external -8O0C). LDA (23.9 mL, 1.1 eq.) was added drop-wise at such rate that the internal temp did not increase more than 30C during addition. The reaction mixture turned into a deep brownish, thick phase and was stirred for 30 minutes at this temperature. TMS-Cl (43.4 mL, 43.45 mmol) was added via syringe in a relatively fast fashion. The reaction became a clear and light yellow solution. LDA (23.9 mL, 1.1 eq.) was added drop-wise in a quicker version, and the reaction mixture was allowed to stir for 2 hours. Methyl 2-methoxyacetate (5.59 mL, 56.48 mmol) was added quickly through a syringe. The reaction mixture was quenched at -780C by adding 20 ml of saturated NH4Cl solution. Evaporation of the organic extracts under reduced pressure gave a colored residue. Purification utilizing ISCO (0-^25% EtOAc/hexanes), gave the title product (3 g). LCMS: 188 [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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); A1;,
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Electric Literature of 40872-87-5, The chemical industry reduces the impact on the environment during synthesis 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, I believe this compound will play a more active role in future production and life.

Methyl 4-chloro-3-cyanobenzoate (2). To a solution of methyl 3-amino-4- chlorobenzoate (15.0 g, 81.0 mmol) in H20/conc. HC1 (150 mL/17 mL), nitrous acid solution (5.6 g, 81 mmol) was added drop-wise at 0C and stirred for 30 min. The reaction mixture was neutralized with sodium hydroxide solution. The resulting diazonium salt solution was added to a solution of cuprous chloride (8.0 g, 81.0 mmol) and sodium cyanide (10.7 g, 218.0 mmol) at 0 C and stirred at room temperature for 4h. The reaction mixture was quenched with water (150 mL) and extracted with ethyl acetate (200 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude obtained was triturated with diethyl ether and n-pentane to yield 2 (8.0 g, 51%) as a white solid. 1H NMR (400 MHz, CDCI3) delta 3.88 (s, 3H), 4.26 (brs, 2H), 7.29 (d, J = 8.2 Hz, 1H), 7.34-7.37 (dd, J =1.9, 8.2 Hz, 1H), 7.45 (d, J = 1.9 Hz, 1H)

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

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; ALEXANDER, Matthew David; MCDONALD, Joseph John; NI, Yike; NIU, Deqiang; PETTER, Russell C.; QIAO, Lixin; SINGH, Juswinder; WANG, Tao; ZHU, Zhendong; WO2014/149164; (2014); A1;,
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Electric Literature of 87808-49-9,Some common heterocyclic compound, 87808-49-9, name is Methyl 2-bromo-4-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.

(2) Compound 2 (4.0 g), Compound 3(3.52 g),[1,1′-bis (diphenylphosphino) ferrocene] palladium (II)Dichloromethane adduct (1.43 g)And potassium carbonate (7.24 g)Of N, N-dimethylformamide (80 mL)Under a nitrogen atmosphere,And the mixture was stirred at 80 C. for 6 hours.To the reaction mixture was added diethyl ether (200 mL)And the mixture was stirred, and insoluble matter was removed by filtration.Water and ethyl acetate were added to the filtrate, followed by stirring,And extracted with ethyl acetate.The obtained organic layer was washed with water and saturated brine,Dried and concentrated under reduced pressure.The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 95: 5 to 80:20) to obtain Compound 4 (2.78 g) As a pale yellow viscous substance.

The synthetic route of 87808-49-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma; Sato, Atsushi; Imashiro, Ritsuo; Tuzisima Tosinori, Shuichi; Tanimoto, Koichi; Yamamoto, Yasuo Wang; Nakane, Tetsuya; Erikawa, Chihiro; (123 pag.)JP2018/199673; (2018); A;,
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