Month: March 2021

Electric Literature of 610-96-8, These common heterocyclic compound, 610-96-8, name is Methyl 2-chlorobenzoate, 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: Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ¡À 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ¡À 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized. The synthetic route of 610-96-8 has been constantly updated, and we look forward to future research findings. Reference:
Article; Malineni, Jagadeesh; Jezorek, Ryan L.; Zhang, Na; Percec, Virgil; Synthesis; vol. 48; 17; (2016); p. 2795 – 2807;,
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Adding a certain compound to certain chemical reactions, such as: 685-88-1, name is Diethyl 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 685-88-1, Computed Properties of C7H11FO4

Example 4 4,6-Dihydroxy-5-fluoropyrimidine 30% sodium methoxide in methanol (63.0 g, 0.35 mol) are rapidly admixed with formamide (33.75 g, 0.75 mol) and the mixture is heated to reflux temperature. At reflux, ethyl fluoromalonate (17.8 g, 95.0 mmol, content: about 95%) is then added over a period of 200 min, and the mixture is stirred at reflux temperature for a further 3 h. The suspension is concentrated completely under reduced pressure, the residue is dissolved in water (65 ml) and the pH of the solution is adjusted to pH 1 using 30% HCl. The resulting precipitate is then filtered off with suction and dried at 100 C. under reduced pressure overnight. This gives 4,6-dihydroxy-5-fluoropyrimidine (12.1 g, content (HPLC-STD): 90.2%; 88.3% of theory) as a solid.

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

Reference:
Patent; Bayer Aktiengesellschaft; US6255486; (2001); B1;,
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Synthetic Route of 73368-41-9, A common heterocyclic compound, 73368-41-9, name is Ethyl 4-amino-3-methoxybenzoate, molecular formula is C10H13NO3, 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.

[0554j Ethyl 4-amino-3-methoxybenzoate (5-C) (3 g, 15.37 mmol) was dissolved in MeCN (10 mL), K2C03 (5.310 g, 38.43 mmol) and ethyl bromide (3.350 g, 30.73 mmol) were added. The solution was stirred at 100C for 24 h in a 30 mL of autoclave. The mixture was filtered and the filtrate was concentrated to afford ethyl 4-(diethylamino)-3- methoxybenzoate (5-D) (392 mg).

The synthetic route of 73368-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALIOS BIOPHARMA, INC.; WANG, Guangyi; BEIGELMAN, Leonid; TRUONG, Anh; NAPOLITANO, Carmela; ANDREOTTI, Daniele; HE, Haiying; WO2014/31784; (2014); A1;,
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Application of 126430-46-4,Some common heterocyclic compound, 126430-46-4, name is Benzyl 4-bromobutanoate, molecular formula is C11H13BrO2, 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.

REFERENCE EXAMPLE 8 A mixture of benzyl 4-bromobutyrate (23.7 g), imidazole (8.1 g), potassium carbonate (14.0 g) and acetone (400 ml) was stirred under reflux for 6 hours. After cooling the mixture to room temperature, the insoluble material was filtered off, and the filtrate was concentrated. The residual oil was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate/methanol (20/1, v/v) gave benzyl 4-(1-imidazolyl)butyrate (7.3 g, 33%) as an oil. NMR (delta ppm in CDCl3): 2.11 (2H,m), 2.34 (2H,t,J=6.8 Hz), 3.99 (2H,t,J=6.8 Hz), 5.12 (2H,s), 6.87 (1H,s), 7.05 (1H,s), 7.30-7.40 (5H,m).

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

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5719157; (1998); A;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 87-13-8 as follows. Recommanded Product: 87-13-8

Compound 23 (4.77 g, 47.7 mmol) was added dropwise to Compound 22 (10 g, 46.3 mmol) with subsurface N2 flow to drive out ethanol below 30 C for 0.5 hours. The solution was then heated to 100-110 C and stirred for 2.5 hours. After cooling the mixture to below 60 C, diphenyl ether was added. The resulting solution was added dropwise to diphenyl ether that had been heated to 228-232 C for 1.5 hours with subsurface N2 flow to drive out ethanol. The mixture was stirred at 228-232 C for another 2 hours, cooled to below 100 C and then heptane was added to precipitate the product. The resulting slurry was stirred at 30 C for 0.5 hours. The solids were then filtered, and the cake was washed with heptane and dried in vacuo to give Compound 25 as a brown solid. 1H NMR (DMSO-d6; 400 MHz) delta 12.25 (s), delta 8.49 (d), delta 8.10 (m), delta 7.64 (m), delta 7.55 (m), delta 7.34 (m), delta 4.16 (q), delta 1.23 (t).

According to the analysis of related databases, 87-13-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; VAN GOOR, Fredrick, F.; WO2013/67410; (2013); A1;,
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Application of 105-53-3, A common heterocyclic compound, 105-53-3, name is Diethyl malonate, molecular formula is C7H12O4, 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: In an atmosphere controlled glovebox, Cu(OTf)2 (398 mg, 1.10 mmol, 2.20 equiv.), arylboroxine (0.330 mmol, 0.670 equiv.), and CsOAc (106 mg, 0.550 mmol, 1.10 equiv.) were added sequentially to a 2 dram vial charged with a stir bar. The sp3-carbon nucleophile (0.500 mmol, 1.00 equiv.) and triethylamine (0.210 mL, 1.50 mmol, 3.00 equiv.) were added as a solution in anhydrous 1,2-DCE (1.20 mL). Additional 1,2-DCE (2¡Á0.5 mL) was used to quantitatively transfer the solution to the reaction mixture. The vial was sealed with a PTFE-lined cap and stirred outside the glovebox at 30 C. Reaction progress was generally monitored by GC-FID using n-dodecane as an internal standard. Unless otherwise noted, reactions were quenched after 36-48 hours, when >95% conversion of sp3-carbon nucleophile was reached. The reaction was quenched with 5 mL of brine and extracted with EtOAc (4¡Á10 mL). The organic layer was then washed with 5 mL brine and dried with Na2SO4, and the solvent was removed by vacuum. The crude residue was purified by flash silica gel chromatography. Note: the order of addition of reagents is important for achieving optimal yields.

The synthetic route of 105-53-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Governors of the University of Alberta; LUNDGREN, Rylan; MOON, Patrick; (56 pag.)US2018/186721; (2018); A1;,
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These common heterocyclic compound, 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, 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. Formula: C5H7BrO2

General procedure: To a 20 mL two-necked round-bottom flask attached with areflux condenser were added V-65 (25 mg, 0.1 mmol) and K2CO3(138 mg, 1.0 mmol), and this flask was purged with argon.Then, 1-nonanal (1a, 71 mg, 0.5 mmol), methyl 2-(bromomethyl)acrylate (2a, 269 mg, 1.5 mmol), and degassedbenzene (5 mL) were added. The mixture was stirred at 60 C for1 h. The reaction mixture was filtered through a short plug ofCelite, and the filtrate was concentrated under reduced pressure.The residue was purified by flash column chromatographyon SiO2 (hexane/EtOAc = 1:0 to 30:1) and preparative HPLC(chloroform) to give methyl 2-methylene-4-oxododecanoate(3b, 101 mg, 84%).

The synthetic route of Methyl 2-(bromomethyl)acrylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kippo, Takashi; Kimura, Yuki; Ueda, Mitsuhiro; Fukuyama, Takahide; Ryu, Ilhyong; Synlett; vol. 28; 14; (2017); p. 1733 – 1737;,
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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. 19063-55-9, name is 6-Bromochromen-2-one, A new synthetic method of this compound is introduced below., Formula: C9H5BrO2

General procedure: Under inert atmosphere (N2), in a 25 mL round bottom flask, Ar3Bi (0.208 mmol; 0.35 eq.), CsF (0.24 g: 1.8 mmol; 3 eq.), PPh3 (0.004 g: 0.018 mmol; 3 mol%), the aryl bromide (0.60 mmol; 1 eq.) was added to DMF (5 mL). The solution was warmed to 90 C prior addition of PEPPSI IPr (0.012 g: 0.018 mmol; 3 mol%). The reaction was monitored by GC/MS to follow the total consumption of the aryl bromide. Cooled to room temperature (RT), the reaction mixture was diluted by addition of diethyl ether (20 mL) and aqueous HCl 6 M (30 mL). After decantation, the aqueous solution was extracted with diethylether (2 * 20 mL). The collected organic phases were then washed with HCl 6 N (2 * 25 mL), water (25 mL) and brine (25 mL) prior drying over MgSO4. After concentration under reduced pressure, the resulting crude product was subjected to purification by column chromatography leading after concentration under reduced pressure to the title compound.

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; Cassirame, Benedicte; Condon, Sylvie; Pichon, Christophe; Journal of Molecular Catalysis A: Chemical; vol. 425; (2016); p. 94 – 102;,
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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. 1214334-90-3, name is Methyl 2-bromo-4-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H6BrF3O2

To a solution of 400 mg (1.413 mmol) 2-bromo-4-trifluoromethyl-benzoic acid methyl ester, 146 mg (1.696 mmol) cyclopropyl boronic acid, 1.21 g (4.946 mmol) tri-potassium phosphate monohydrate, 40.9 mg (0.141 mmol) tricyclohexyl phosphine in 6 ml toluene and 0.3 ml water under nitrogen at room temperature, was added 15.9 mg (0.0707 mmol) palladium acetate. The mixture was stirred in a 100 C. oil bath for 4 hours and overnight at room temperature under nitrogen. The mixture was cooled to room temperature. Water was added and the mixture extracted with ethyl acetate. The organic layer was washed once with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 10%) to provide 0.24 g (71%) of the title compound as a yellow oil.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1214334-90-3.

Reference:
Patent; Kolczewski, Sabine; Pinard, Emmanuel; Stalder, Henri; US2010/197715; (2010); A1;,
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Related Products of 17100-63-9,Some common heterocyclic compound, 17100-63-9, name is Methyl 4-bromo-3-methoxybenzoate, molecular formula is C9H9BrO3, 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: The methyl benzoate (200-1500 mg), PdCl2(CH3CN)2 (0.02 eq)and SPhos (0.08 eq) were added to a pressure tube. Then, 1,4-dioxane (0.5-3.5 mL) and Et3N (0.5-2 mL) were added under N2 atmosphere, followed by dropwise addition of HBpin (1.5 eq) while stirring under N2 atmosphere. The reaction mixture was heated to 80 C and stirred for 5-20 h. After cooling to rt, the reaction mixturewas filtered through a Celite pad. If further purificationwasperformed, it is specified in each specific example. 4.6.3 Methyl 3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate fx9 The target compound was prepared as described in Section 4.6 , starting with methyl 4-bromo-3-methoxybenzoate (501 mg, 2.05 mmol). The crude oil (600 mg) was used without further purification. 1H NMR spectroscopy confirmed the presence of 54% of the desired product by comparison with the literature [54] . 1H NMR (600 MHz, DMSO-d6) delta: 7.65-7.63 (m, 1H), 7.54-7.52 (m, 1H), 7.44-7.43 (m, 1H), 3.86 (s, 3H), 3.80 (s, 3H), 1.28 (s, 12H).

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-bromo-3-methoxybenzoate, its application will become more common.

Reference:
Article; Bugge, Steffen; Buene, Audun Formo; Jurisch-Yaksi, Nathalie; Moen, Ingri Ullestad; Skj¡ãnsfjell, Ellen Martine; Sundby, Eirik; Hoff, Bard Helge; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 255 – 274;,
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