Month: May 2021

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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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. 1195768-18-3, name is Methyl 3-amino-2-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 1195768-18-3

Step A: methyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-2-fluorobenzoate: Methyl 3-amino-2-fluorobenzoate (50 g, 1 eq) was charged to reactor followed by dichloromethane (250 mL, 5 vol). The contents were stirred and cooled to -15 C and pyridine (26.2 mL, 1.1 eq) was added. After addition of the pyridine, the reactor contents were adjusted to ~15C and the addition of 2,6-diflurorobenzenesulfonyl chloride (39.7 mL, 1.0 eq) was started via addition funnel. The temperature during addition was kept <25 C. After complete addition, the reactor contents were warmed to 20-25 C and held overnight. Ethyl acetate (150 mL) was added and dichloromethane was removed by distillation. Once distillation was complete, the reaction mixture was then diluted once more with ethyl acetate (5 vol) and concentrated. The reaction mixture was diluted with ethyl acetate (10 vol) and water (4 vol) and the contents heated to 50-55 C with stirring until all solids dissolve. The layers were settled and separated. The organic layer was diluted with water (4 vol) and the contents heated to 50-55 C for 20-30 min. The layers were settled and then separated and the ethyl acetate layer was evaporated under reduced pressure to ~3 volumes. Ethyl Acetate (5 vol.) was added and again evaporated under reduced pressure to ~3 volumes. Cyclohexane (9 vol) was then added to the reactor and the contents were heated to reflux for 30 min then cooled to 0 C. The solids were filtered and rinsed with cyclohexane (2 x 100 mL). The solids were air dried overnight to obtain methyl 3- {[(2,6-difluorophenyl)sulfonyl]amino}-2-fluorobenzoate (94.1 g, 91%). According to the analysis of related databases, 1195768-18-3, the application of this compound in the production field has become more and more popular. Reference:
Patent; NOVARTIS AG; CAPONIGRO, Giordano; HORN-SPIROHN, Thomas; LEHAR, Joseph; (49 pag.)WO2017/37587; (2017); A1;,
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Electric Literature of 10076-48-9,Some common heterocyclic compound, 10076-48-9, name is Methyl 2,2-dimethoxypropanoate, molecular formula is C6H12O4, 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.

EXAMPLE 14 Methyl 2-cinnamyloxyiminopropionate 2.8 g. (15 mmol) O-cinnamylhydroxylamine hydrochloride in 20 ml. water are added to 2.8 g. (19 mmol) methyl 2,2-dimethoxypropionate in 100 ml. water. The mixture is left to stand for 2 days, with occasional shaking, and the resultant oil then extracted with methylene chloride. The extracts are dried and evaporated. As residue, there are obtained 3.3 g. (94% of theory) methyl 2-cinnamyloxyiminopropionate in the form of a colorless oil. The ester can be saponified with a methanolic solution of potassium hydroxide to give 2-cinnamyloxyiminopropionic acid; m.p. 89-91 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2,2-dimethoxypropanoate, its application will become more common.

Reference:
Patent; Boehringer Mannheim GmbH; US4425360; (1984); A;,
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Related Products of 178312-47-5, 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 178312-47-5 as follows.

(Reference Example 1) 4,4-Difluorocyclohexanecarboaldehyde To a solution of 173 g (0.900 mol) of 4,4-difluorocyclohexanecarboxylic acid ethyl ester in 1.0 L toluene, 945 ml (0.945 mol) of 1.0 M diisobutyl aluminum hydride-toluene solution was added dropwise at -55C or lower temperatures and then the reaction solution was stirred at -65C for 30 minutes. After completion of the reaction, saturated ammonium chloride aqueous solution was added at -40C or lower temperatures to the reaction solution and then 1.0 L of 4 N hydrochloric acid was added at 0C or lower temperatures. The organic layer was separated and then the aqueous layer was extracted with toluene, and the combined organic layers were washed with 1 N hydrochloric acid, saturated sodium hydrogencarbonate aqueous solution and saturated sodium chloride aqueous solution in order and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained oily residue was subjected to distillation under reduced pressure (55-57C/6 mmHg) to provide 75.3 g of the title compound as a colorless oil (yield: 57%). 1H-NMR spectrum (300 MHz, CDCl3) delta ppm: 9.68 (1H, d, J = 1 Hz), 2.42-2.28 (1H, m), 2.16-1.70 (8H, m).

According to the analysis of related databases, 178312-47-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Daiichi Sankyo Company, Limited; UBE Industries, Ltd.; KAWAI, Yukinori; IWASE, Noriaki; KIKUCHI, Osamu; TAKATA, Katsunori; MOTOYAMA, Takahiro; HAGIHARA, Masahiko; EP2801574; (2014); A1;,
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Synthetic Route of 2901-13-5, 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. 2901-13-5, name is Ethyl 2-methyl-2-phenylpropanoate, This compound has unique chemical properties. The synthetic route is as follows.

4-Iodo-(1′-carboxy-1′-methyl)ethylbenzene. A mixture of (1′-ethoxycarbonyl-1′-methyl)ethylbenzene (28.0 g, 146 mmol), iodine (24.7 g), sodium iodate (7.1 g) and concentrated sulfuric acid (4 ML) in acetic acid (200 ML) was stirred and heated at 55 C for 90 hours.. The solvent was evaporated and the residue was partitioned between water and hexane.. The organic phase was washed with aqueous sodium thiosulfate, dried, filtered, and evaporated.. The residue was taken up in ethanol (200 ML) and water (100 ML), and potassium hydroxide (20 g) was added.. The mixture was heated under reflux for 5 hours, and cooled to rt.. The mixture was washed with hexane.. The aqueous phase was acidified with concentrated hydrochloric acid, and extracted with hexane.. The organic phase was dried, filtered and evaporated to give 4-iodo-(1′-carboxy-1′-methyl)ethylbenzene as a solid (19.6 g, 67 mmol, 46%).

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-methyl-2-phenylpropanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; EP1171113; (2004); B1;,
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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. 141-12-8, name is (Z)-3,7-Dimethylocta-2,6-dien-1-yl acetate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 141-12-8

General procedure: A two-neck round bottom flask was charged with Rh2(OAc)4 (4.4 mg, 0.01 mmol), and alkene (1.0 mmol) followed by addition of acetone (3.0 mL). A dry-ice condenser was attached to the flask, then, isobutyraldehyde (274 muL, 3.0 mmol) was added; and a constant flow of oxygen was introduced to the system via an oxygen-filled balloon. Reaction completion was monitored by GC-MS. When the reaction was complete, solvent was removed under reduced pressure and the oily residue was separated by flash chromatography using ether-hexanes solvent mixtures. All epoxide product spectroscopic data were in accord with literature data.

According to the analysis of related databases, 141-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shabashov, Dmitry; Doyle, Michael P.; Tetrahedron; vol. 69; 47; (2013); p. 10009 – 10013;,
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