Author: Jessica.F

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. 66315-16-0, name is Methyl 3-amino-4-(methylamino)benzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H12N2O2

Methyl 3-amino-4-(methylamino)benzoate (0.49 g, 2.75 mmol) in DMF (5 ml) was added to a solution of 4-benzyloxybenzoic acid (0.62 g, 2.75 mmol) in DMF (4 ml) at 0 C. Subsequently, HOAt (0.4 g, 3.0 mmol) and WSCI-HCl (0.58 g, 3.0 mmol) were added to the former solution at 0 C and stirred at 20 C for 15 h. The reaction mixture was quenched with sat. NH4Cl and extracted with CH2Cl2. The combined extracts were washed with H2O and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by the silica gel column chromatography to give 2-1 in 58% yield.

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 66315-16-0.

Reference:
Article; Fujimori, Ko; Iguchi, Yusuke; Yamashita, Yukiko; Gohda, Keigo; Teno, Naoki; Molecules; vol. 24; 22; (2019);,
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Synthetic Route of 335599-07-0,Some common heterocyclic compound, 335599-07-0, name is Ethyl 3-oxa-bicyclo[3.1.0]hexane-6-carboxylate, molecular formula is C8H12O3, 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.

(3-Oxa-bicyclo[3.1.0]hex-6-yl)-methanol (56)-A 1M solution of LiAlH4 in THF (16.77 mL, 16.77 mmol) was cooled in an ice-water/acetone bath and a solution of 56 (2.62 g, 16.77 mmol) in THF (25 mL) was added slowly with stirring. The reaction was warmed to RT over 30 min and stirred for 1 h. The reaction was quenched by slow portionwise addition of 4.8 g of Na2SO4.10H2O, Stirring was continued for additional 1 h after the vigorous reaction subsided. MgSO4 was added and solids were removed by filtration, rinsed with fresh THF and solvents evaporated. The residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (0 to 50% EtOAc) to afford 0.98 g (51.3%) of 56 as a colorless liquid.

The synthetic route of 335599-07-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rotstein, David Mark; Melville, Chris Richard; US2008/249087; (2008); A1;,
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17100-63-9, name is Methyl 4-bromo-3-methoxybenzoate, 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: 17100-63-9

To a stirred solution of methyl 4-bromo-3-methoxybenzoate (11.2 g) in THF (130 mL), methanol (45 mL) and water (45 mL) was added a 1 M solution of lithium hydroxide in water (140 mL). The mixture was stirred at room temperature for 1 h. The solvent was removed in vacuum. Water was added and 1 N hydrochloric acid was added with ice bath cooling until pH 4 was reached. The precipitated solid was collected by filtration, washed with water and dried in vacuum to give 10.1 g of the title compound, that was used without further purification. 1H-NMR (300MHz, DMSO-d6): delta [ppm]= 3.87 (s, 3H), 7.42 (dd, 1 H), 7.50 (d, 1 H), 7.68 (d, 1 H), 13.21 (br. s., 1 H).

The synthetic route of 17100-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; KOSEMUND, Dirk; WENGNER, Antje Margret; SIEMEISTER, Gerhard; STOeCKIGT, Detlef; BRUENING, Michael; WO2013/87579; (2013); A1;,
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Related Products of 57381-59-6, These common heterocyclic compound, 57381-59-6, name is Methyl 5-bromo-2-fluorobenzoate, 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.

Compound 46b (24.00 g, 102.99 mmol) was dissolved in methanol (300 mL), and N,N-dimethylformamide (100 mL), triethylamine (100 mL), and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (12.62g, 15.45 mmol) were added. The reaction mixture was stirred under a carbon monoxide atmosphere (50 psi) for 16 hr at 80 C, filtered, concentrated under reduced pressure, and extracted with ethyl acetate (500 mL×2). The organic phases were combined, dried, concentrated under reduced pressure to dryness, and purified by silica gel column chromatography (petroleum ether/ethyl acetate=100-0%), to give Compound 46c (11.00 g). 1H NMR (400 Hz, CDCl3) delta 3.95(s, 3H), 3.97(s, 3H), 7.20-7.24 (m, 1H), 8.21-8.23 (m, 1H), 8.63-8.65 (m, 1H). MS-ESI calculated value [M+ H]+ 213, measured value 213.

The synthetic route of 57381-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; YAO, Yuanshan; CHEN, Bin; CHEN, Yuan; LI, Ao; XU, Ran; HUANG, Zhensheng; TIAN, Dongdong; LI, Hongwei; YANG, Chengshuai; LI, Jian; CHEN, Shuhui; (102 pag.)EP3489233; (2019); A1;,
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Application of 37466-90-3, 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. 37466-90-3, name is Ethyl 3,4-diaminobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The mixture of ethyl 3,4-diaminobenzoate 19 (1 eq., 27.7 mmol) and appropriate benzoic acid (1 eq.,27.7 mmol) and 20 mL of polyphosphoric acid was heated at 140 C for 3 h. Warm reaction mixture was poured onto ice covered with excess of solid NaHCO3 and then 60 mL of AcOEt were added. Aqueous phase was extracted with AcOEt (4×70 mL). Extracts were dried over Na2SO4 and concentrated. The crude product was purified by chromatography on silica gel (eluent heptane/AcOEt, 0-60 % or CHCl3/MeOH 0-5 %).

The chemical industry reduces the impact on the environment during synthesis Ethyl 3,4-diaminobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Moszczy?ski-P?tkowski, Rafa?; Majer, Jakub; Borkowska, Ma?gorzata; Bojarski, ?ukasz; Janowska, Sylwia; Mat?oka, Miko?aj; Stefaniak, Filip; Smuga, Damian; Bazyd?o, Katarzyna; Dubiel, Krzysztof; Wieczorek, Maciej; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 96 – 116;,
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Synthetic Route of 18448-47-0, These common heterocyclic compound, 18448-47-0, name is Methyl cyclohex-1-enecarboxylate, 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: 4-Trifluoromethylbenzonitrile oxide (4) was generated as follows: a solution of the corresponding chloroxime (0.25g, 1.12mmol) in dry dichloromethane was passed through an Amberlyst-21 column and added dropwise over 30min to the solution of a dipolarophile in dry dichloromethane, and the solution was stirred overnight at room temperature. Water was added, organic layer was separated and the aqueous one extracted with dichloromethane. The combined organic layers were dried (MgSO4) and the product was purified by flash column chromatography.

Statistics shows that Methyl cyclohex-1-enecarboxylate is playing an increasingly important role. we look forward to future research findings about 18448-47-0.

Reference:
Article; Gucma, Miros?aw; Go??biewski, W. Marek; Michalczyk, Alicja K.; Journal of Molecular Structure; vol. 1060; 1; (2014); p. 223 – 232;,
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Synthetic Route of 121-98-2, These common heterocyclic compound, 121-98-2, name is Methyl 4-methoxybenzoate, 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.

The mixture of 4-methoxy methyl benzoate (33 g, 0.2 mol) and anhydrous hydrazine (7.7 g, 0.24 mmol) was heated to 140 C under nitrogen atmosphere, and reacted at the said temperature for 30 minutes. After cooled to the room temperature, the mixture was extracted with ethyl acetate (3×100 ml). The organic layer was dried over anhydrous sodium sulfate, and filtered, then concentrated under reduced pressure to give a crude product of intermediate compound 19 (30 g), which can be used for the next reaction step directly.

The synthetic route of 121-98-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Foreland Biopharma Co., Ltd.; ZHANG, Xingmin; WANG, Ensi; GUO, Jing; NIU, Shengxiu; DAI, Zhuolin; ZHENG, Nan; JI, Liping; WANG, Zhenfang; LIANG, Tie; EP2860176; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 431-47-0, name is Methyl 2,2,2-trifluoroacetate, 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 431-47-0, Formula: C3H3F3O2

4-bromo-1-(secbutyl)-1H-pyrazole (1.0 g, 5.0 mmol) was dissolved in dry THF (15 mL) at -78 C under nitrogen and was stirred for 10min. n-BuLi (2.5 M in hexanes, 2.1 mL, 5.2 mmol) was added drop wise to the solution was stirred for 2 h at -78 C. After two hours, methyl trifluoroacetate (0.85 mL, 8.5 mmol) was added drop wise and stirred for 30 min at -78 C. The solution was then allowed to warm up to room temperature and let stir for overnight. The mixture was then quenched with NH4Cl (20mL) and extracted with ether (50 mL), and dried over MgSO4. After concentration in vacuo(note: remove shortly after the ether is removed, because the compound is quite volatile), the residue was purified with flash chromatography over silica gel (hexane: ether = 98:2) to yield the product as a liquid.

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, Methyl 2,2,2-trifluoroacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Camerino, Eugene; Wong, Dawn M.; Tong, Fan; Koerber, Florian; Gross, Aaron D.; Islam, Rafique; Viayna, Elisabet; Mutunga, James M.; Li, Jianyong; Totrov, Maxim M.; Bloomquist, Jeffrey R.; Carlier, Paul R.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 20; (2015); p. 4405 – 4411;,
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Some common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, molecular formula is C9H9BrO2, 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. SDS of cas: 99548-54-6

[000576] Synthesis of 9: [000577] A mixture of 7 (228 mg, 1.0 mmol), 8 (288 mg, 1.4 mmol), Na2C03 (212 mg, 2 mmol) and Pd(PPh3)4 (115 mg, 0.10 mmol) in 2 mL of toluene, 2 mL of ethanol and 2 mL of water was stirred under N2 protection at 80 C for 17 hours concentrated in vacuo. The residue was diluted with ethyl acetate (50 mL), washed with water (30 mL) and brine (30 mL), dried over anhydrous Na2S04 and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (ethyl acetate: petroleum ether = 1 : 50) to give 9 as white oil (260 mg, yield: 83.8%). LC-MS m/z: 311.1 [M+H]+. LC-MS Purity (214 nm): > 96%; tR = 2.256 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 99548-54-6, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James; ERB, Michael; QI, Jun; (96 pag.)WO2016/196879; (2016); A1;,
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Reference of 41841-16-1,Some common heterocyclic compound, 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, molecular formula is C9H9BrO2, 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 methyl 2-(4-bromophenyl)acetate (1 g, 4.36 mmol) in dry THF (20 mL)was added LiHMDS (5.23 mL, 1 M) dropwise at -78 C under N2. The mixture was stirred at 0C for 2 h. After Mel (1.23 g, 8.72 mmol) was added at -78 C, the mixture was stirred at 20 Cfor 16 h. Quenched with NH4C1 sat. and extracted with EtOAc. The organic was concentratedand purified by silica gel colunm (PE/EtOAc = 1/0 to 100/1) to give the title product (642 mg,yield 6 1%). MS (ES+) C10H11BrO2 requires: 243, found 244 [M+H].

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-(4-bromophenyl)acetate, its application will become more common.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BROOIJMANS, Natasja; BRUBAKER, Jason, D.; FLEMING, Paul, E.; HODOUS, Brian, L.; KIM, Joseph, L.; WAETZIG, Josh; WILLIAMS, Brett; WILSON, Douglas; WILSON, Kevin, J.; (347 pag.)WO2017/181117; (2017); A1;,
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