Month: March 2021

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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 3-(dimethylamino)acrylate

General procedure: All microwave reactions were carried out in a capped (10 mL) microwave-vessel (Borosilicate glass vial sealed) that was placed in a microwave cavity. The pressure was set at 17 bar (average of an effective pressure = 4 bar) with power 75 W. DIEA (3.4 g, 3.4 mmol) was added to a solution of either 2,5-difluoro-4-(pyrrolidin-1-yl) benzoylchloride 12 (0.83 g, 3.4 mmol) or 2,5-difluoro-4-(pyrrolidin-1-yl)benzothioyl chloride 13 (0.88 g, 3.4 mmol) and ethyl-3-(diethylamino)acrylate 14 (0.45 g, 3.1 mmol) in acetonitrile (5 mL). The mixture reaction was held at 100 C for 20 min. After the reaction vessel was cooled to room temperature, the crude product was diluted with water (10 mL) and extracted with ethyl acetate(3 ¡Á 10 mL). The organic layers were combined, dried over Na2SO4, filtered, evaporated and purified by a flash column chromatography (eluent n-hexane: acetone, 3:1)to give the titled compounds. Ethyl-2-(2,5-difluoro-4-(pyrrolidin-1-yl)benzoyl)-3-(dimethylamino) acrylate (15)Yellow oil (Rf = 0.3), Yield 85%. IR (KBr) numax in cm-1:2993 (C-H, Ar), 2953 (C-H), 1760 (C=O), 1692 (C=O),1654 (C=C, Ar), 1592 (C-N). 1H NMR (400 MHz, DMSOd6):delta = 7.77 (1H, s, CH), 7.32 (1H, d, J = 5.0 Hz, CH-Ar),6.88 (1H, d, J = 5.2 Hz, CH-Ar), 4.2 (2H, q, J = 7.1 Hz,CH2), 3.47-3.42 (4H, m, 2CH2), 3.1 (6H, s, 2CH3), 2.01-1.97 (4H, m, 2CH2), 1.32 (3H, t, J = 4.2 Hz, CH3).

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Almashal, Faeza A.; Alshawi, Jasim M.; Dhumad, Adil M.; Jassem, Ahmed M.; Medicinal Chemistry Research; (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. 685-88-1, name is Diethyl fluoromalonate, A new synthetic method of this compound is introduced below., SDS of cas: 685-88-1

General procedure: All flasks and stirrer bars were flame dried before use. Tothe N-oxide (0.2 mmol, 1.0 equiv.), dissolved in 2 cm3dichloromethane was added Tf2O (0.3 mmol, 1.5 equiv.) at0 C. In another flask, a suspension of NaH (0.7 mmol, 3.5equiv.) in 1 cm3 tetrahydrofuran was cooled to 0 C andthe malonate (0.7 mmol, 3.5 equiv.) was added. After15 min, the malonate solution was added to the activatedN-oxide solution and the mixture was stirred at roomtemperature for 1 h. The reaction was quenched withNH4Cl solution and the aqueous phase was extracted withdichloromethane. The combined organic layers werewashed with brine before being dried over MgSO4. Thesolvents were removed under reduced pressure and thecrude product was purified by column chromatography.

The synthetic route of 685-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Erratum; Lemmerer, Miran; Teskey, Christopher J.; Kaiser, Daniel; Maulide, Nuno; Monatshefte fur Chemie; vol. 149; 4; (2018); p. 721 – 722;,
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Related Products of 5941-55-9, These common heterocyclic compound, 5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate, 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.

A mixture of ethyl-5-amino-1H-pyrazole-4-carboxylate (20.0 g, 129 mmol), (E)-ethyl 3-ethoxyacrylate (22.4 mL, 155 mmol) and cesium carbonate (63.0 g, 193 mmol) in DMF (322 mL) was stirred at 110 C. overnight. After being cooled to 0 C., the reaction mixture was acidified with 2 N aq. HCl. A precipitated solid was collected by filtration and washed with water and EtOAc to afford ethyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate (24.7 g, 92%) as a pale yellow solid. 1H-NMR (DMSO-d6, Varian, 400 MHz): delta 1.27 (3H, t, J=7.2 Hz), 4.80 (2H, q, J=6.8 Hz), 6.16 (1H, d, J=8.0 Hz), 8.14 (1H, s), 8.58 (1H, d, J=8.0 Hz), 11.7 (1H, br. s).

The synthetic route of 5941-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HANDOK INC.; CMG Pharmaceutical Co., Ltd.; Kim, Moonsoo; Lee, Chaewoon; Lee, Gilnam; Yoon, Cheolhwan; Seo, Jeongbeob; Kim, Jay Hak; Lee, Minwoo; Jeong, Hankyul; Choi, Hyang; Jung, Myung Eun; Lee, Ki Nam; Kim, Hyun Jung; Kim, Hye Kyoung; Lee, Jae Il; Lee, MinWoo; Kim, Misoon; Choi, Soongyu; (124 pag.)US2016/168156; (2016); A1;,
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Application of 64123-77-9,Some common heterocyclic compound, 64123-77-9, name is Methyl 2-(3-fluorophenyl)acetate, molecular formula is C9H9FO2, 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.

(ab) from methyl m-fluorophenylacetate and methyl formate there was obtained methyl 2-(m-fluorophenyl)-3-hydroxy-acrylate of b.p. 75-81/0.1 mm;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-(3-fluorophenyl)acetate, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; US4735940; (1988); A;,
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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. 89-71-4, name is Methyl 2-methylbenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 89-71-4

General procedure: To a solution of 6.0 g (0.04 mol) of methyl 2-methylbenzoate derivatives in 38 mL of chloroform, 7.5 g (0.042 mol) of N-bromosuccinimide and 0.078 g of benzoyl peroxide were added and carefully warmed up to 65 C until reaction started. Then the mixture was refluxed for 5 h. After cooling down to room temperature, the deposit of succinimide was filtered. The solvent was removed under reduced pressure and the crude product was used in the next step without further purification. To a solution of functionalized methyl 2-(bromomethyl)benzoate (6.55 mmol), substituted phenol (8.5 mmol), K3PO4 (16.4 mmol) and toluene 20 mL were added to Schlenk under argon. The resulting solution was stirred to 110 C for 5 h. The progress of the reaction was monitored by TLC. The mixture was extracted with EtOAc, washed with water, brine and the combined organic layers were dried over anhydrous Na2SO4and the solvent was removed under reduced pressure. The crude product was used in the next step without further purification. To the solution of the ester (0.015 mol) in MeOH (73 mL), was added 13 mL aqueous KOH (20%) and refluxed at 80C for 5 h. MeOH was removed and the aqueous phase was washed with DCM. After acidifying with HCl (10%) the deposit was collected and washed with water.

The synthetic route of 89-71-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Scoccia, Jimena; Castro, M. Julia; Faraoni, M. Belen; Bouzat, Cecilia; Martin, Victor S.; Gerbino, Dario C.; Tetrahedron; vol. 73; 20; (2017); p. 2913 – 2922;,
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Synthetic Route of 5121-34-6, 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. 5121-34-6 name is Methyl 2-amino-3-methoxybenzoate, 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 b] To a solution of compound 2 (86.7 g, 473 mmol) in N,N-dimethylformamide (430 mL) was added N-bromosuccinimide over 15 min under ice-cooling, and the mixture was stirred for 1 hr. To the reaction solution were added saturated aqueous sodium hydrogen carbonate solution (500 mL) and water (500 mL), and the mixture was extracted with ethyl acetate (1.0 L). The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography, and suspended and washed in n-hexane (120 mL) to give compound 3 (108 g, 88.1 %). 1H-NMR (400 MHz, CDCl3)delta: 3.87(6H, s), 6.03(2H, brs), 6.90(1H, d, J=2.0Hz), 7.26(1H,s), 7.60(1H, d, J=2.4Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-3-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; TAKAHASHI, Taichi; UMINO, Akinori; IIJIMA, Daisuke; TAKAMATSU, Hisayuki; (173 pag.)EP3135667; (2017); A1;,
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Reference of 59247-47-1, 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. 59247-47-1, name is tert-Butyl 4-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a 100 mL round-bottom flask purged and maintained under an inert atmosphere of nitrogen was added (1S,4S,5R)-5-[[l-cyclopropyl-4-(2,6-dichlorophenyl)-1H-l,2,3-triazol-5- yl]methoxy]-2-azabicyclo[2.2.1]heptane 621 (45 mg, 0.12 mmol, 1.00 equiv.), toluene (20 mL), tert-butyl 4-bromobenzoate (45.7 mg, 0.18 mmol, 1.50 equiv), BINAP (15 mg, 0.02 mmol, 0.20 equiv.), Cs2CO3 (116 mg, 0.36 mmol, 3.00 equiv.), and Pd2(dba)3 (11 mg, 0.01 mmol, 0.10 equiv.). The resulting mixture was heated for at 1 10¡ãC for 2 days. After cooling to room temperature, solids were filtered out, and the filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1 : 10 to 1 :5, and to 1 :3). Removal of solvents afforded tert-butyl 4-[(1S,4S,5R)-5-[[l- cyclopropyl-4-(2,6-dichlorophenyl)-1H-l,2,3-triazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptan- 2-yl]benzoate 70a (40 mg, 61percent) as a light brown oil.

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

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5326-50-1, name is Ethyl 2-(1-hydroxycyclohexyl)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 5326-50-1, name: Ethyl 2-(1-hydroxycyclohexyl)acetate

To a solution of X4 (510 mg) in MeOH was added IN aqueous NaOH. The reaction mixture was stirred at 600C for Ih5 and then concentrated in vacuo. The residue was diluted with water, washed with Et2O and the aqueous layer acidified with IN aqueous citric acid and extracted with EtOAc. The organics were dried (MgSO4) and concentrated in vacuo to yield after recrystallization compound X5 (220mg): 1H-NMR (CDCl3, 500MHz) 3.63 (s, IH), 2.45 (s, 2H), 1.22-1.64 (m, 10H) ppm; FIA m/z 157.2 ES”.

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 2-(1-hydroxycyclohexyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/25307; (2007); A2;,
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Synthetic Route of 25597-16-4,Some common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, molecular formula is C6H7F3O2, 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 LiAlH4 (1.35g, 35.5mmol, 1.5equiv.) in dry Et2O (13.0mL) under argon atmosphere was added dropwise a solution of AlCl3 (2.22g, 16.6mmol, 0.7equiv.) in dry Et2O (6.5mL). After 20min of stirring at 0C, a solution of ethyl (E)-4,4,4-trifluorocrotonate (4.00g, 23.8mmol, 1.0 equiv.) in dry Et2O was added dropwise. The resulting mixture was allowed to stir at 0C for 2 h. A saturated aqueous solution of Na2SO4 was then added (Caution: very exothermic reaction). The mixture was filtrated and the solid was washed several times with Et2O. The organic layers were combined and washed with brine and dried over MgSO4. Solvent was removed by thorough distillation at atmospheric pressure to afford (E)-4,4,4-trifluorobut-2-en-1-ol (7) as a colorless oil which was used without any further purification.

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

Reference:
Article; Forcellini, Elsa; Hemelaere, Remy; Desroches, Justine; Paquin, Jean-Francois; Journal of Fluorine Chemistry; vol. 180; (2015); p. 216 – 221;,
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Reference of 431-47-0, These common heterocyclic compound, 431-47-0, name is Methyl 2,2,2-trifluoroacetate, 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.

Phthalimide (100 mg, 0.68 mmol), DMSO (10 mL), CH3ONa (112 mg, 2 mmol, 3 eq.) was added to the reaction flask in turn, stirred at room temperature for 5 minutes, and then uniformly dispersed after NaH. Methyl trifluoroacetate (0.28 mL, 2.7 mmol, 4 eq.) was slowly injected into the reaction flask. After reacting for 10 hours, the TLC was plated, and the starting point disappeared, that is, the reaction was completed, and the stirring was stopped. Extract twice with ethyl acetate and distilled water, then wash with saturated NaCl solution. The organic phases were combined, and the organic phase was dried over anhydrous magnesium sulfate. The magnesium sulfate was removed by filtration, and the solvent was evaporated. Purification by column chromatography gave white solid N-methylphthalimide (109 mg,Yield 100%).

The synthetic route of 431-47-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Petrochemical College; Xiao Duoduo; Zheng Xin; Zeng Jiechun; Huang Jiawei; Zhou Rujin; Guan Ying; Liang Jieling; (8 pag.)CN109369506; (2019); A;,
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