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. 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 35450-36-3

Example 1; Part A: Compound 1 (20.0 g, 81.61 mmol), trimethylboroxine (13.36 ml_, 97.93 mmol),Pd(dppf)CI2 (1.0 g, 1.36 mmol), dioxane (350 ml_), water (50 ml_), and cesium carbonate (22.5 g, 163 mmol) were stirred at 110 0C (oil bath) under nitrogen for 16 hours. After cooling, the solid was removed by filtration. The solution was concentrated and purified by sgc (10:1 EtOAc/hexanes) to give 2 (12.1 g,80%).

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

Reference:
Patent; SCHERING CORPORATION; KOZLOWSKI, Joseph, A.; YU, Wensheng; WONG, Michael, K.C.; KIM, Seong-Heon; TONG, Ling; LAVEY, Brian, J.; SHANKAR, Bandarpalle, B.; YANG, De-Yi; FELTZ, Robert; KOSINSKI, Aneta, Maria; ZHOU, Guowei; RIZVI, Razia, K.; DAI, Chaoyang; FIRE, Luke; GIRIJAVALLABHAN, Vinay, M.; LI, Dansu; POPOVICI-MULLER, Janeta; RICHARD, Judson, E.; ROSNER, Kristin, E.; SIDDIQUI, M., Arshad; YANG, Liping; WO2010/54279; (2010); 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. 1236357-65-5, name is Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 1-(4-bromophenyl)cyclobutanecarboxylate

Methyl 1-(4-bromophenyl)cyclobutanecarboxylate under nitrogen atmosphere(1.3 g, 4.8 mmol), (R)-3-oxo hexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxylic acid tert-butyl ester (1.2 g, 4.8 mmol),Tris(dibenzylideneacetone)dipalladium(440mg, 0.48mmol),2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (410 mg, 0.97 mmol) and cesium carbonate (3.1 g, 9.5 mmol) were dissolved.In 1,4-dioxane (30 mL). The reaction was carried out at 90 C for 12 h.The heating was stopped, the solid was filtered off, and the filtrate was concentrated under reduced pressure.The residue obtained was subjected to silica gel column chromatography(PE/EA(V/V)=4/1)Purified to give the title compound as a white solid(770 mg, 37%).

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Liu Xinchang; Huang Jianzhou; Zhang Yingjun; S ·geerdeman; (267 pag.)CN109111451; (2019); A;,
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Reference of 69812-51-7, These common heterocyclic compound, 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, 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 stirred solution of 5-amino-l,3-dihydro-2H-benzo[d]imidazol-2-one50 (50 mg) in pyridine (0.5 ml) was added methyl 4-(chlorosulfonyl)benzoate 163 (78.7 mg). The reaction mixture was stirred at room temperature for 1 h. LC-MS analysis indicated that the reaction was complete. The reaction mixture was poured into EtOAc/THF (1 :3) and extracted sequentially with diluted 2 M aq. HCl and with saturated brine. The organic layer was dried over Na2S04 and concentrated in vacuo. The residue was taken up in dichloromethane and the mixture was ultrasonicated at room temperature. The mixture was then filtered through sintered glass, and the solid was dried in vacuo to afford methyl 4-(N-(2-oxo-2,3-dihydro-lH-benzo[d]imidazol-5- yl)sulfamoyl)benzoate (101 mg, 87 %) as an off-white solid. MS (ISP): 348.1 ([M+H]+).

Statistics shows that Methyl 4-chlorosulfonylbenzoate is playing an increasingly important role. we look forward to future research findings about 69812-51-7.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GOERGLER, Annick; NORCROSS, Roger; DEY, Fabian; KUSZNIR, Eric Andre; (206 pag.)WO2019/43217; (2019); A1;,
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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 110661-91-1 as follows. Application In Synthesis of tert-Butyl 4-bromobutanoate

To a mechanically stirred solution of terf-butyl 4-bromobutanoate [CAS 1 10661 – 91 -1] (42.3 g, 0.19 mol) in DMF (600 mL) was added in portions a solid mixture of 3-amino-5-methoxyphenol [CAS 162155-27-3] (26.4 g, 0.19 mol) and Cs2CO3 (123.6 g, 0.379 mol). The reaction was stirred at 60C for 65 h, and allowed to reach room temperature. The mixture was poured out into H2O (2.5 L). The product was extracted with Et2O (2 times). The combined organic layers were washed with brine, dried over MgSO4 and filtered off. The solvent was evaporated under reduced pressure, and then co-evaporated with toluene. The residue was purified via Normal Phase HPLC (Stationary phase: silica gel 60A 25-40 muiotatauiota (Merck), Mobile phase: gradient from 20% EtOAc, 80% heptane to 60% EtOAc, 40% heptane) yielding te/t-butyl 4-(3-amino-5-methoxyphenoxy)butanoate 1a (27 g).

According to the analysis of related databases, 110661-91-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; KESTELEYN, Bart Rudolf Romanie; RABOISSON, Pierre Jean-Marie Bernard; BONFANTI, Jean-Francois; BARDIOT, Dorothee Alice Marie-Eve; MARCHAND, Arnaud Didier M; (74 pag.)WO2017/167951; (2017); A1;,
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2905-69-3, name is Methyl 2,5-dichlorobenzoate, 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: 2905-69-3

General procedure: The following procedure is representative of these reactions. PhSH (5 mmol) and t-BuOK (5.1 mmol) were added to 250 mL of distilled liquid ammonia; PhS- ions were ready for use. The substrate, methyl 2,5-dichlorobenzoate (1 mmol), was added to the solution, and the reaction mixture was irradiated for 2 h. The reaction was then quenched with an excess of ammonium nitrate (or methyl iodide), and the ammonia was allowed to evaporate. The solid was dissolved in water, and HNO3 was added to the water phase to reach pH=3 before extraction with diethyl ether. Products were isolated by column chromatography employing silica gel and quantified by GC using the internal standard method.

The synthetic route of 2905-69-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Uranga, Jorge G.; Montanez, Juan P.; Santiago, Ana N.; Tetrahedron; vol. 68; 2; (2012); p. 584 – 589;,
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Related Products of 15964-79-1, A common heterocyclic compound, 15964-79-1, name is Methyl 2-(3,4-dimethoxyphenyl)acetate, molecular formula is C11H14O4, 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.

l-(4-Bromophenyl)-4-(3,4-dimethoxyphenyl)butane-l,3-dione; Sodium hydride (60% dispersion, 3.80 g, 95.1 mmol) was added portionwise to methyl 2-(3,4-dimethoxyphenyl)acetate (10 g, 47.6 mmol) in Et2O (100 ml) at O0C. A solution of 4′-bromoacetophenone (9.48 g, 47.6 mmol) in Et2O (50 ml) was added dropwise over 1 h. The mixture was heated at reflux for 16 h, cooled, poured into ice/HCl (2 M), extracted with Et2O (3 x 100 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was crystallized from MeOH to give the title compound (9 g, 50 %) as a tan powder.

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; ESSILOR INTERNATIONAL (COMPAGNIE GENERALE D’OPTIQUE); ALPHAMICRON, INC.; WO2008/30226; (2008); A1;,
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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. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 2-amino-5-bromobenzoate

To a solution of compound 28-6 (2.1 g, 9.17 mmol) in THF (20 mL) was added a aqueous solution of NaOH (2.1 g, 20 mL). At the end of the addition, the mixture was stirred at 60 C overnight. After the reaction was completed, the THF solvent was removed. The residue was dissolved in EtOAc (50 mL) and washed with water (50 mL x 3). The combined aqueous phase was adjusted to pH 4 with hydrochloric acid (1 M) and the solid was precipitated. The resulting mixture was filtered to give the title compound as a pale yellow solid (1.42 g, 72%). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) mlz: 217 [M+H] +; and ln NMPv (400 MHz, CDC13) delta (ppm): 7.59 (d, 1H, J= 8.0 Hz), 6.96 (d, 1H, J= 1.6 Hz), 6.64 (dd, 1H, J= 8.0 Hz, 2.0 Hz).

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 52727-57-8.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; XIE, Hongming; REN, Qingyun; LI, Shifeng; FU, Changping; HU, Bailin; WU, Xiwei; TANG, Changhua; WO2014/82380; (2014); A1;,
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Application of 53518-15-3, 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. 53518-15-3 name is 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, 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.

A vial was charged with S5 (9 mg, 0.011 mmol), 7-amino-4-(trifluoromethyl) coumarin (7 mg, 0.033 mmol, 3 eq.), HATU (12 mg, 0.033 mmol, 3 eq.), DIEA (19 1iL, 0.11 mmol, 10 eq.) and DIvIF (300 1iL). Contents were stirred at room temperature and ambient atmosphere for 24 h, after which the solvent was concentrated to dryness, and the crude product was purified by silica gel chromatography (0-5% MeOH/DCM, linear gradient) to afford PC-3F549-exHT (2 mg, 18%).?H NMR (CDC13, 400 MHz) 8.05 (d, J 7.9 Hz, 1H), 7.92 (d, J= 8.0 Hz, 1H), 7.49 (m, 2H), 7.30 (dd, J 8.9, 2.1 Hz, 1H), 7.17 (d, J= 2.1 Hz, 111), 6.79 (s, 1H), 6.65 (s, 1H), 6.57 (d, J 8.6 Hz, 2H), 6.12 (d, J 2.3 Hz, 2H), 6.02 (dd, J= 8.6, 2.3 Hz, 2H), 5.23 (s, 1H), 4.14 (s, 2H), 3.89 (t, J 7.3 Hz, 811),3.67 -3.50 (m, 18H), 3.45 (t, J 6.6 Hz, 211), 3.33 (d, J= 5.6 Hz, 2H), 2.37 (p, J= 7.2 Hz, 4H),1.77 (p,J= 6.7 Hz, 2H), 1.60 (d, J= 14.6 Hz, 2H), 1.44 (q, J 8.1, 6.8 Hz, 2H), 1.37 (d, J 7.0 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, and friends who are interested can also refer to it.

Reference:
Patent; HOWARD HUGHES MEDICAL INSTITUTE; LAVIS, Luke; JRADI, Fadi, M.; (109 pag.)WO2018/182811; (2018); A1;,
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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. 820236-81-5, name is Methyl 2-bromo-6-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H6BrFO2

Synthesis of methyl 2-[4-[2-[4-(2,2-dimethylpropyl)-1-trityl-imidazol-2-yl]ethyl]phenyl]-6-fluoro-benzoate (14): a mixture of 13 (5.17 g, 9.17 mmol), bis-pinacolatodiboron (3.06 g, 12.1 mmol), [1,1?-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (0.38 g, 0.47 mmol) and KOAc (2.74 g, 27.9 mmol) in dioxane (100 mL) was stirred under reflux for 8 h. After the reaction mixture was concentrated, the residue was dissolved in EtOAc and water, then filtered through a Celite pad. The organic layer was washed with brine, dried (Na2SO4), concentrated and purified by column chromatography (hexane:EtOAc = 5:1) to provide the boronate ester as a pale yellow solid (5.17 g, 92%). A mixture of the boronate ester (8.92 g, 14.6 mmol), methyl 2-bromo-6-fluoro-benzoate (4.42 g, 19.0 mmol), Pd(PPh3)4 (1.69 g, 1.46 mmol) and 2 M Na2CO3 (22 mL, 44 mmol) in DMF (170 mL) was stirred at 100 C for 7 h. The mixture was concentrated and diluted in ethylacetate, washed with water, dried (Na2SO4), concentrated and purified by column chromatography (hexane:EtOAc = 3:1) to provide 14 as a pale yellow amorphous (6.54 g, 71%) 1H NMR (CDCl3) delta: 7.43-7.36 (1H, m), 7.35-7.29 (9H, m), 7.16-7.10 (9H, m), 7.10-7.04 (1H, m), 6.84 (2H, d, J = 8.2 Hz), 6.35 (1H, s), 3.61 (3H, s), 2.45-2.40 (4H, m), 2.31-2.25 (2H, m), 0.93 (9H, s). MS (APCI) m/z: 637 (M+H)+.

According to the analysis of related databases, 820236-81-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kiyotsuka, Yohei; Shimada, Kousei; Kobayashi, Shozo; Suzuki, Masanori; Akiu, Mayuko; Asano, Masayoshi; Sogawa, Yoshitaka; Hara, Takashi; Konishi, Masahiro; Abe-Ohya, Rie; Izumi, Masanori; Nagai, Yoko; Yoshida, Kazuhiro; Abe, Yasuyuki; Takamori, Hideo; Takahashi, Hisashi; Bioorganic and Medicinal Chemistry Letters; vol. 26; 17; (2016); p. 4205 – 4210;,
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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 152849-72-4 as follows. category: esters-buliding-blocks

A mixture of methyl 5-bromo-2,4-dimethyl-benzoate (400 mg, 1.65 mmol), LiOH (197 mg, 8.21 mmol) in tetrahydrofuran (3 mL) and water (3 mL) was stirred under N2 at 70 C. for 3 h. The reaction was then diluted with 30 mL of water and 20 mL of EtOAc. The mixture was then adjusted pH to 4-5 with 1N HCl. The organic layer was concentrated to dryness to give the title compound as a white solid (350 mg, 92.9% yield). LCMS (ESI) [M+H]+=230.9.

According to the analysis of related databases, 152849-72-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
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