Category: esters-buliding-blocks

51760-21-5, name is Dimethyl 5-bromoisophthalate, 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. SDS of cas: 51760-21-5

Example 110A Dimethyl 2′-chlorobiphenyl-3,5-dicarboxylate Under argon, 500 mg (1.83 mmol) of dimethyl 5-bromoisophthalate together with 429 mg (2.75 mmol) of 2-chlorophenylboronic acid were dissolved in 8 ml of toluene, and 72 mg (0.18 mmol) of 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl, 84 mg (0.09 mmol) of tris(dibenzylideneacetone)dipalladium and 777 mg (3.66 mmol) of potassium phosphate were added successively. The mixture was heated to 110 C. and stirred at this temperature for 20 h. For work-up, the reaction mixture was allowed to cool to RT and diluted with 20 ml of ethyl acetate. The solid was filtered off with suction and the residue was washed three times with in each case 10 ml of ethyl acetate. The combined filtrates were washed twice with in each case 10 ml of water. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified chromatographically [Method 19]. This gave 305 mg (55% of theory) of the target compound. LC/MS [Method 4]: Rt=1.24 min; MS [EIpos]: m/z=305 (M+H)+ 1H-NMR (400 MHz, DMSO-d6): delta=3.92 (s, 6H), 7.46-7.55 (m, 3H), 7.60-7.68 (m, 1H), 8.23 (d, 2H), 8.52 (t, 1H).

The synthetic route of 51760-21-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Furstner, Chantal; Keldenich, Joerg; Delbeck, Martina; Kolkhof, Peter; Kretschmer, Axel; Pluschkell, Ingo; Pook, Elisabeth; Schmeck, Carsten; Trubel, Hubert; US2013/190330; (2013); A1;,
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Related Products of 103-25-3, A common heterocyclic compound, 103-25-3, name is Methyl 3-phenylpropionate, molecular formula is C10H12O2, 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.

27.1. methyl 2-benzyl-3-oxopropanoate To a mixture of 3 g (18.3 mmol) of methyl 3-phenylpropanoate and 3.57 mL (54.8 mmol) of methyl formate in 36 mL of toluene, under argon, are added dropwise successively 54.8 mL (54.8 mmol) of a 1 M solution of TiCl4 in toluene, 0.17 mL (0.91 mmol) of trimethylsilyl trifluoromethanesulfonate and 19.6 mL (82.2 mmol) of tributylamine. The medium is then heated for 2 hours 30 minutes at 60 C. and stirred for 12 hours at room temperature. The reaction medium is hydrolysed with 200 mL of water and extracted with 200 mL of Et2O. The organic phase is dried over Na2SO4, filtered and concentrated under reduced pressure. 3.12 g of methyl 2-benzyl-3-oxopropanoate are obtained in the form of an oil, which is used without further purification in the following step. Yield=87%

The synthetic route of 103-25-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI; US2011/294788; (2011); 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. 6520-83-8, name is Ethyl 2-methoxy-6-methylbenzoate, A new synthetic method of this compound is introduced below., Product Details of 6520-83-8

Step 1 Ethyl 2-bromomethyl-6-methoxybenzoate 19.56 g of N-bromosuccinimide and 4.84 g of benzoyl peroxide were added to a solution of 19.40 g of ethyl 2-methoxy-6-methylbenzoate in 150 ml of carbon tetrachloride. The reaction medium was refluxed for 6 hours (no further change). The reaction medium was cooled to 5 C. and the succinimide was filtered. The organic phase was washed with a saturated sodium hydrogen carbonate solution (2*150 ml), dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel (column puriFlash, IR-50SI/800G, Spot II) eluted with heptane/ethyl acetate (gradient). 15.5 g of ethyl 2-bromomethyl-6-methoxybenzoate were obtained in the form of a yellow oil which later crystallizes. Yield=56%.

The synthetic route of 6520-83-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Musicki, Branislav; Aubert, Jerome; Boiteaux, Jean-Guy; Clary, Laurence; Rossio, Patricia; Schuppli-Nollet, Marlene; US2014/309208; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 35598-05-1, name is Methyl 4-methoxy-2-methylbenzoate, 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 35598-05-1, Application In Synthesis of Methyl 4-methoxy-2-methylbenzoate

To a solution of methyl 4-methoxy-2-methylbenzoate (1 g, 5.6 mmol) in CC14 (25 mL) was added dropwise N-bromosuccinimide (1.1 g, 6.2 mmol) previously dissolved in CCI4 (5 mL) and a catalytic amount of benzoylperoxide. The mixture was refluxed for 2 hours, cooled to room temperature and poured onto ice water. The aqueous mixture was extracted with DCM (3x), and the combined organics were dried over MgS04, filtered, and concentrated in vacuo to provide 2.1 g of the titled product as light yellow solid (~ 100% yield): [M+H+] m/z 260.

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Reference:
Patent; SELEXAGEN THERAPEUTICS, INC.; VERNIER, Jean-Michel; MAY, John; O’CONNOR, Patrick; RIPKA, William; PINKERTON, Anthony; WO2011/85261; (2011); A1;,
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35615-97-5, name is Methyl 4-bromonaphthalene-1-carboxylate, 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. SDS of cas: 35615-97-5

A stirred solution of methyl 4-bromo-I-naphthoate (Collect. Czech. Chem. Commun. 1997, 62(11), 1737; 7.3g, 28mmole) in degassed toluene (300ml) was treated with hexamethylditin (10g, 31mmole) and tetrakis(triphenylphosphine)palladium(0) (720mg) and heated at reflux under argon for 3h.. On cooling, the mixture was filtered through Celite (Diatomaceous Earth), concentrated under vacuum and the residue chromatographed on silica gel eluding with 0-3% ether/60-80 petrol to afford the title compound as a colourless oil (9.06g, 94%)

The synthetic route of 35615-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham plc; EP1216239; (2004); B1;,
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Related Products of 6279-86-3,Some common heterocyclic compound, 6279-86-3, name is Triethyl methanetricarboxylate, molecular formula is C10H16O6, 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: 4.1.1.1 Ethyl 1-hexyl-1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxylate (2a); A mixture of N-hexylaniline (0.88g, 5mmol) and triethyl methanetricarboxylate 3 (3.48g, 15mmol) was irradiated with microwaves at the fixed power of 250 Watt (max temp 250C) for 20min in open vessel conditions. The crude mixture was directly purified by flash chromatography (PE/AcOEt 4:1) giving compound 2a as a yellow oil. (0.856g, 54% yield). 4.1.1.5 Ethyl 1-methyl-1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxylate (2e) Yield: 35%. 1H NMR: (200 MHz, CDCl3): delta 12.64 (bs, 1H), 7.30-7.26 (m, 4H), 4.35 (q, 2H, J = 7.3 Hz), 3.62 (s, 3H), 1.19 (t, 3H, J = 7.3 Hz). ES-MS: 270 [M+Na]+.

The synthetic route of 6279-86-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Manetti, Fabrizio; Petricci, Elena; Gabrielli, Annalisa; Mann, Andre; Faure, Helene; Gorojankina, Tatiana; Brasseur, Laurent; Hoch, Lucile; Ruat, Martial; Taddei, Maurizio; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 747 – 757;,
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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. 13412-12-9, name is Methyl 3-(methylamino)but-2-enoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Methyl 3-(methylamino)but-2-enoate

Step 2: 2-(4-Bromo-benzoyl)-3-[(E)-methylimino] -butyric acid methyl ester; [00439] 4-Bromobenzoyl chloride (17.14g, 78.1mmol) and 3-methylamino-but-2-enoic acid methyl ester (10. Og, 78.1mmol) were combined in THF (60OmL) and cooled to O0C. Pyridine (6.8mL, 85.9mmol) was added by syringe, and the reaction was stirred overnight at room temperature. Solid pyridine hydrochloride was observed on the flask walls, so the solution was decanted and then concentrated to 10% of its original volume. The residue was diluted with EtOAc (40OmL) and washed twice with H2O. The organic layer was dried, filtered, and concentrated to give the title compound.

The synthetic route of 13412-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMIRA PHARMACEUTICALS, INC.; HUTCHINSON, John Howard; SEIDERS, Thomas Jon; ARRUDA, Jeannie M.; WO2010/68775; (2010); A2;,
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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. 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H8BrNO2

To a 250 mL round bottom flask equipped with a magnetic stir bar was added N,N-dimethylformamide or benzenesulfonyl chloride.Stir the solution for 20 minutes.The color of the solution turned pale yellow.Add methyl 4-amino-3-bromobenzoate,The mixture was stirred at room temperature for 30 minutes.A large amount of solid product is formed, and the solid is filtered.Wash with ether and dry in vacuo.The resulting solid was then transferred to another 250 mL round bottom flask and neutralized by the addition of NaOH solution and ethyl acetate. Transfer the solution to the funnel for separation.The inorganic layer was extracted with 2 x 100 mL of ethyl acetate.After merging the organic layers,It was washed with brine and dried over anhydrous sodium sulfate for 3 hr.That is, the intermediate 1 [(E)-N-(2-bromo-4-carbomethoxyphenyl)-N,N-dimethylformamidine].

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; Zaozhuang College; Shandong Lunan Mei Chemical Engineering Technology Institute; Liu Xuejing; Han Ying; Yan Peng; Bie Fusheng; Shi Yijun; Cao Han; (12 pag.)CN110183384; (2019); A;,
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Synthetic Route of 35450-36-3, A common heterocyclic compound, 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, molecular formula is C9H9BrO3, 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.

Add CuI (19.45 mg), PdCl2 (PPh3) 2 (105.29 mg) to the round bottom flask,Under nitrogen, methyl 2-bromo-5-methoxybenzoate (1.68 mL), phenylacetylene (0.66 mL), Et3N (2.08 mL), and THF (15 mL) were added in this order, and the reaction was performed at 55 C for 6 h.TLC tracks the progress of the reaction; after the reaction is complete, the resulting reaction solution is cooled to room temperature,Then filtered through diatomaceous earth and purified by column chromatography to obtain the first intermediate;Dissolving the first intermediate in methanol, adding a 10% NaOH solution, and stirring at room temperature for 2 h,TLC tracks the progress of the reaction; after the reaction is complete, adjust the pH of the resulting reaction solution to dilute 2-3 with dilute hydrochloric acid,The obtained solid was filtered and purified by recrystallization to obtain a second intermediate;Add SOCl2 to the second intermediate and reflux at 90 C for 2 h.TLC followed the progress of the reaction; after the reaction was completed, SOCl2 was removed to obtain a third intermediate;At 0 C, add N-methoxyamine and potassium carbonate to 15 mL of ethyl acetate in this order.(EA) and water (EA: water volume ratio = 2: 1), the third intermediate was added dropwise after 10 min, and the reaction was performed at room temperature for 1 h.TLC tracks the progress of the reaction; after the reaction is complete, it is extracted with EA and H2O.Dry over anhydrous sodium sulfate and recrystallize to obtain N-methoxy-5-methoxy-2-phenylethynylbenzamide (1h);

The synthetic route of 35450-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hunan University of Science and Technology; Xie Wenlin; Liu Renzhi; Qiu Guanyinsheng; (15 pag.)CN110590641; (2019); A;,
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Reference of 6091-64-1, These common heterocyclic compound, 6091-64-1, name is Ethyl 2-bromobenzoate, 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.

Ethyl 2-bromobenzoate (1g, 4.37mmol) prepared from Step 1 wasdissolved in toluene (20 mL) and ethanol (4mL) mixed solution, and then theretowere added 4-fluorophenyl boronic acid (672mg, 4.80mmol), potassium carbonate(1.21g, 8.73mmol) and tetrakis (triphenylphosphine) palladium (504mg,0.44mmol). The reaction was stirred at 100 deg. C 6 hours, cooled to roomtemperature and filtered through Celite. The reaction was concentrated underreduced pressure to remove the solvent. Then washed with water and extracted ethyl acetate. Theorganic layer was dried over anhydrous magnesium sulfate, filtered andconcentrated. The resulting residue was purified by column chromatography toproduce the title compound (948mg, 89%).

Statistics shows that Ethyl 2-bromobenzoate is playing an increasingly important role. we look forward to future research findings about 6091-64-1.

Reference:
Patent; East Asia ST Corporation; Jin, Shunhui; Ren, Yuanbin; Cao, Zonghuan; Cui, Shangao; Pu, Zhengxiang; Jin, Miyan; Cui, Chenghe; Lee, Mingjing; Zhao, Kangxun; (182 pag.)CN105555761; (2016); A;,
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