Tag: M.W=200-300

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. 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, A new synthetic method of this compound is introduced below., Formula: C10H11BrO2

A solution of 25g ethyl (4-bromophenyl)acetate in100 ml DMF was added dropwise to 13.8 gpotassium-tert.butylate in 150 ml DMF at 0C and stirred for additional 30 minat 0C. Then 18.4 g bromocyclopentane were added dropwise at 0C and the reactionmixture was stirred until reaction completion. The mixture was given on water,extracted with EE, the combined organic layers washed with water and brine,dried with Na2SO4, filtered and evaporated to dryness.Yield: 35.6 g, used without further purification in the next step.

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; Koppitz, Marcus; Braeuer, Nico; Ter Laak, Antonius; Irlbacher, Horst; Rotgeri, Andrea; Coelho, Anne-Marie; Walter, Daryl; Steinmeyer, Andreas; Zollner, Thomas M.; Peters, Michaele; Nagel, Jens; Bioorganic and Medicinal Chemistry Letters; vol. 29; 18; (2019); p. 2700 – 2705;,
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Synthetic Route of 87-13-8, The chemical industry reduces the impact on the environment during synthesis 87-13-8, name is Diethyl 2-(ethoxymethylene)malonate, I believe this compound will play a more active role in future production and life.

A mixture of aniline (25.6 g, 0.275 mol) and diethyl 2-(ethoxymethylene)malonate (62.4 g, 0.288 mol) was heated at 140-150 C for 2 h. The mixture was cooled to room temperature and dried under reduced pressure to afford 2-phenylaminomethylene-malonic acid diethyl ester as a solid, which was used in the next step without further purification. ‘H NMR (DMSO-rfc) d 11.00 (d, 1H), 8.54 (d, J = 13.6 Hz, 1H), 7.36-7.39 (m, 2H), 7.13-7.17 (m, 3H), 4.17-4.33 (m, 4H), 1.18-1.40 (m, 6H).

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, Diethyl 2-(ethoxymethylene)malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; LEE, Elaine Chungmin; NAVAMAL, Mettachit; NTI-ADDAE, Kwame Wiredu; SHI, Yi; SHRESTHA, Muna; ZHANG, Beili; ZWICKER, Carl; (263 pag.)WO2019/191620; (2019); A1;,
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Electric Literature of 756525-95-8, These common heterocyclic compound, 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, 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.

To a dried scintillation vial containing a magnetic stir bar was added tert-butyl 4-oxopiperidine-1-carboxylate (399 mg, 2 mmol), H2N-PEG2-COOt-Bu (550 mg, 2.4 mmol), 4 A molecular sieves (activated powder, 200 mg), and 1,2-dichloroethane (5 mL). The mixture was stirred for 1 h at room temperature. To the reaction mixture was added sodium triacetoxyborohydride (845 mg, 4 mmol). The mixture was stirred for 3 days at room temperature. The resulting mixture was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 850 mg of compound 211 as a viscous oil. MS (ESI) mlz: [M+HjCalcd for C21H41N206 417.3; Found 417.2.

The synthetic route of 756525-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; R.P. SCHERER TECHNOLOGIES, LLC; RABUKA, David; MCFARLAND, Jesse M.; DRAKE, Penelope M.; BARFIELD, Robyn M.; (195 pag.)WO2017/83306; (2017); A1;,
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These common heterocyclic compound, 75567-84-9, name is Methyl 3-(4-bromophenyl)propanoate, 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. Safety of Methyl 3-(4-bromophenyl)propanoate

To a 100 mL two-neck flask were added (R) -tert-butyl 3-oxohexahydroimidazo [1, 5-a] pyrazine-7 (1H) -carboxylate (228 mg, 0.95 mmol) , methyl 3- (4-bromophenyl) propionate (230 mg, 0.95 mmol) , tris (dibenzylideneacetone) dipalladium (87 mg, 0.095 mmol) , 2-di-tert-butylphosphino-2′, 4′, 6′-triisopropylbiphenyl (80 mg, 0.19 mmol) , cesium carbonate (0.62 g, 1.89 mmol) and 1, 4-dioxane (10 mL) . The mixture was stirred at 90 for 2 hours, and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 1/1) to give the title compound as a white solid (171 mg, 45%) . MS (ESI, pos. ion) m/z: 426.1 [M+Na] +.

The synthetic route of Methyl 3-(4-bromophenyl)propanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Xinchang; REN, Qingyun; YAN, Guanghua; GOLDMANN, Siegfried; ZHANG, Yingjun; (253 pag.)WO2019/76310; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 56441-97-5, name is Methyl 4-(benzyloxy)-3-methoxybenzoate, 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 56441-97-5, Quality Control of Methyl 4-(benzyloxy)-3-methoxybenzoate

A 250 mL, round-bottomed flask with a stirring bar, a solution of 4-hydroxy-3-methoxybenzoic acid (20 g, 118.94 mmol) was added slowly to a solution of methanol (100 mL) and concentrated sulfuric acid (10 mL). After being stirred for 12 h at reflux, saturated solution of sodium bicarbonate was added to adjust the pH to 7. Dichloromethane was added and the mixture was then filtered and the organic phase evaporated on a rotary evaporator and to obtain the compound 2 (20.37 g, 94 %). Compound 2 (20.4 g, 111.98 mmol) was added into a 500 mL, round-bottomed flask with a stirring bar, then benzyl bromide (18 mL), potassium carbonate (22 g, 156.8 mmol), DMF (200 mL) were added. It was stirred for 6 h at 80 C. Then the reaction system was poured into right amount of water, white solid (3) was obtained by filtration (28.97 g, 95 %). Compound 3 (16.54 g, 60.74 mmol) was dissolved in CH3COOH (50 mL) and then added into a 250 mL, round bottomed flask with a stirring bar. Then HNO3 (25 mL) was added into the system slowly to keep the temperature of the reaction above 5 C. The reaction temperature was raised to 50 C and kept for another 2 h. After that the system was poured into water and pale yellow solid (I) was obtained6-8 (18.3 g, 95%, m.p.: 134-135 C).

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; Wang, Kai; Zhang, Xiu-Qin; Zhu, Jian; Chen, Qiang; Zhang, Zhong-Qiang; Fan, Li; Asian Journal of Chemistry; vol. 27; 7; (2015); p. 2647 – 2650;,
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Related Products of 99548-54-6, These common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, 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: Aryl halide (1.0 mmol), arylboronic acid (1.2 mmol), K2CO3 (2.0 mmol), Pd(at)Al2O3-agarose (100 mg) and EtOH (5 mL) were added to a Schlenk flask. The mixture was stirred at room temperature under air. Upon complete consumption of starting materials as determined by TLC analysis, the solid was filtered and washed with acetone (3 × 5 mL). The combined organic solvents were concentrated in vacuum to afford product which was purified by silica gel column chromatography (petroleum ether/EtOAc = 10:1).

Statistics shows that Methyl 3-bromo-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 99548-54-6.

Reference:
Article; Wang, Peng; Cai, Jin; Chen, Junqing; Ji, Min; Journal of the Brazilian Chemical Society; vol. 26; 4; (2015); p. 748 – 754;,
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Synthetic Route of 87-13-8, 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. 87-13-8, name is Diethyl 2-(ethoxymethylene)malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of aniline (25.6 g, 0.275 mol) and diethyl 2- (ethoxymethylene)malonate (62.4 g, 0.288 mol) was heated at 140- 150 C for 2 h. The mixture was cooled to room temperature and dried under reduced pressure to afford 2- phenylaminomethylene-malonic acid diethyl ester as a solid, which was used in the next step without further purification. XH NMR (DMSO-ifc) delta 11.00 (d, 1H), 8.54 (d, = 13.6 Hz, 1H), 7.36-7.39 (m, 2H), 7.13-7.17 (m, 3H), 4.17-4.33 (m, 4H), 1.18- 1.40 (m, 6H).

The synthetic route of Diethyl 2-(ethoxymethylene)malonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HASELTINE, Eric L.; MOSKOWITZ, Samuel; ROBERTSON, Sarah; WALTZ, David; (169 pag.)WO2019/18395; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 1186-73-8, name is Trimethyl methanetricarboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 1186-73-8

Step 1: Methyl l-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-9-tosyl-2,5,6,9-tetrahydro- 1H-pyrido[2′,3′:4,5]thiepino[3,2-f]indole-3-carboxylate o a stirring solution of Intermediate 9 (1.02 g, 2.75 mmol), (2,4-dimethoxyphenyl)methanamine (0.51 g, 0.45 mL, 3.03 mmol), triethylamine (0.83 g, 1.14 mL, 8.25 mmol) in CH2C12(6.0 mL) at 0 C was added a solution of TiCl4(1M in CH2C12,1.4 mL, 1.4 mmol) dropwise. After the addition, the mixture was brought to roomtemperature and stirred overnight. The reaction was quenched with satd. NaHC03solution (3 mL) and the mixture was diluted with CH2C12(12 mL). The CH2C12layer was separated and the aqueous layer was extracted with CH2C12(2 x 3 mL). The combined organics were evaporated to dryness followed by the addition of trimethyl methanetricarboxylate (1.05 g,5.5 mmol) and diphenyl ether (5.0 mL). The mixture was stirred at 230 C for 10 min, then cooled to room temperature and loaded directly onto a silica gel column. The product was chromato graphed (ethyl acetate in CH2C120-50 %) to furnish the title compound as a light brown solid (1.10 g, 62%). LC-MS: 647.2 [M+H]+, RT 1.57 min.

The synthetic route of 1186-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; ZHANG, Nanjing; ZHANG, Xiaoyan; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Marla, L.; (229 pag.)WO2016/25932; (2016); A1;,
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Electric Literature of 54535-22-7,Some common heterocyclic compound, 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate, molecular formula is C14H17NO4, 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: A diphenyl ether solution of 2e-k (4 mmol) containingcatalytic 2-chlorobenzoic acid was heated by microwaveirradiation (250 C) for 1-2 h. After cooling, the reactionmixture was filtered and the precipitate 3e-k was washedwith n-hexane and water. Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate (3e) Starting from 2e (5 g); Yield (cream powder): 3 g (75 %); m.p. 261-262 C; IR (KBr) numax 1400-1600 (aromatic), 1695(carbonyl), 3150 (N-H) cm-1; LC-MS (ESI) m/z 218.1 (M+H+), 240.1 (M+Na+); Calcd. for C12H11NO3: C, 66.35; H,5.10; N, 6.45. Found: 66.47; H, 5.22; N, 6.27.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diethyl 2-((phenylamino)methylene)malonate, its application will become more common.

Reference:
Article; Hajimahdi; Zabihollahi; Aghasadeghi; Ashtiani, S. Hosseini; Zarghi; Medicinal Chemistry Research; vol. 25; 9; (2016); p. 1861 – 1876;,
Ester – Wikipedia,
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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. 6279-86-3, name is Triethyl methanetricarboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C10H16O6

Example 2N-r(7-hvdroxy-5-oxo-4,5-dihvdropyrazolori,5-alpyrimidin-6-yl)carbonyllglvcine A mixture of lH-pyrazol-5-amine (0.20 g, 2.40 mmol), triethyl methanetricarboxylate (0.51 mL, 2.40 mmol), glycine (0.27 g, 3.60 mmol) and l,8-diazabicyclo[5.4.0]undec-7-ene (0.68 mL, 4.80 mmol) in ethanol (5.0 mL) was heated to 180 0C for 20 minutes in a Biotage Initiator microwave synthesizer. The mixture was purified via preparative HPLC (YMC 75 X 30 mm column, 0.1% TFA in water and 0.1% TFA in acetonitrile) to afford the title compound as a yellow solid (0.065 g, 11%). 1H NMR (400 MHz, OMSO-d6) delta ppm 13.0 (s, 2 H) 9.87 (t, J=5.6 Hz, 1 H) 7.85 (d, J=2.0 Hz, 1 H) 6.01 (d, J=LO Hz, 1 H) 4.16 (d, J=5.8 Hz, 2 H). MS(ES+) m/e 253 [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; SMITHKLINE BEECHAM CORPORATION; WO2009/39323; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics