Month: June 2021

These common heterocyclic compound, 369-26-6, name is Methyl 3-amino-4-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. Recommanded Product: Methyl 3-amino-4-fluorobenzoate

To a solution of imidazo[1 ,2-a]pyridine-3-carboxylic acid (1 ) (10 g, 61 .73 mmol) in dichloromethane (300 ml_) was added DMF (2 ml_) and oxalyl chloride (18 g, 141 .73 mmol) at 0-10 °C. The resulting solution was stirred overnight at room temperature and concentrated under vacuum. The solid obtained was added into a solution of methyl 3- amino-4-fluorobenzoate (7) (10 g, 59.17 mmol) and TEA (20 g, 198.02 mmol) in dichloromethane portionwise. The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum and diluted with of methanol (250 ml_). The solids were collected by filtration and washed with sat. Na2C03 (2×200 ml_) and methanol (2×50 ml_) to yield methyl 4-fluoro-3-(imidazo[1 ,2-a]pyridine-3- carboxamido)benzoate (8) as a light yellow solid.

The synthetic route of Methyl 3-amino-4-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; NOVARTIS PHARMACEUTICALS UK LIMITED; LIANG, Fang; GIBNEY, Michael; YEH, Vince; LI, Xiaolin; MOLTENI, Valentina; SHAW, Duncan; BERMAN, Ashley Mitchell; LEWIS, Sarah; LOREN, Jon; FURMINGER, Vikki; WO2013/33620; (2013); 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 40872-87-5 as follows. Product Details of 40872-87-5

Triethylamine (1.16 g, 11.5 mmol) was added to a mixture of 7-methoxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-3-carboxylic acid (from Example 15 supra) (2.3 g, 10.45 mmol) and HATU (4.37 g, 11.5 mmol) in dry DMF (30 mL). The resulting mixture was stirred at room temperature until clear solution was obtained. 3-Amino-4-chloro-benzoic acid methyl ester (2.32 g, 12.55 mmol) was added and the resulting mixture was stirred for another 20 hours. The reaction mixture was diluted with water (300 mL), aqueous saturated NaHCO3 (60 mL) and ethyl acetate (150 mL). After thorough mixing, off white precipitate was collected by filtration, washed water, ethyl acetate and MeOH, and dried under reduced pressure to give 4-chloro-3-[(7-methoxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-3-carbonyl)-amino]-benzoic acid methyl ester as an off-white solid. (Yield 2.9 g, 71.8%). 1H NMR (300 MHz, d6-DMSO) delta 12.42 (s, 1H), 9.18 (s, 1H), 9.01 (s, 1H), 8.91 (s, 1H), 7.70 (d, 2H, J=1.1 Hz), 6.61 (s, 1H), 3.95 (s, 3H), 3.89 (s, 3H). LC-MS: [M+H]+ 388.

According to the analysis of related databases, 40872-87-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Luk, Kin-Chun; US2012/184562; (2012); A1;,
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Related Products of 18595-14-7, These common heterocyclic compound, 18595-14-7, name is Methyl 4-amino-3-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.

A mixture of compound 1 (429 mg, 0.0026 mol) and NBS (0.7 g, 0.0039 mol) in DCM was stirred at r.t. for 3 h. The mixture was concentrated to a residue, which was purified by Prep-TLC to obtain compound 2 (522 mg, 83%) as a light yellow solid

The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; van Duzer, John H.; Mazitschek, Ralph; US2014/128391; (2014); A1;,
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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. 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C9H9BrO2

To a stirred solution of 100 g methyl-(4-bromophenyl)acetate(9, 0.436 mol) in 300 cm3 tetrahydrofuran, 95 g sodium methoxide (1.75 mol) was added at 0-5 C and maintained for 1 h. 80 g dimethyl carbonate (0.88 mol)was added at 0-5 C over a period of 2 h. The reaction mass was maintained at 25-30 C until the completion ofthe reaction (monitored by HPLC). After completion of the reaction, tetrahydrofuran was concentrated under reduced pressure at 45 C to obtain the syrup. The syrup was diluted in 500 cm3 water and the product was extracted in250 cm3 dichloromethane. The organic layer was concentrated under reduced pressure at 45 C to obtain the thick solution which was dissolved in 200 cm3 isopropyl alcoholat 70 C and maintained for 1 h. The solution was cooled to 0 C and maintained for 60 min. The obtained solid was filtered, washed with isopropyl alcohol, and dried at 50-55 C for 4-6 h to provide 10. Yield: 80 g; purity by HPLC: 99%; m.p.: 72-76 C. The spectral data of compound 10 were found to agree with the reported data [8].

The synthetic route of 41841-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jagtap, Kunal M.; Niphade, Navnath C.; Gaikwad, Chandrashekhar T.; Shinde, Gorakshanath B.; Toche, Raghunath B.; Joshi, Divyesh R.; Mathad, Vijayavitthal T.; Monatshefte fur Chemie; vol. 149; 3; (2018); p. 653 – 661;,
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Some common heterocyclic compound, 27798-60-3, name is Methyl 2-Methoxyphenylacetate, molecular formula is C10H12O3, 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. name: Methyl 2-Methoxyphenylacetate

Triflic acid (7.3 mL, 43.4 mmol) was added dropwise to a solution of thioxanthone oxide (5.00 g, 21.7 mmol) and methyl 2-(2-methoxyphenyl)acetate (4.31 g, 23.9 mmol) in DCM (60 mL) at -78 C. and slowly warmed to 25 C. overnight. The reaction mixture was quenched with water (100 mL), the layers separated, and the aqueous phase washed with water (4×100 mL) and concentrated to a crude solid. The crude solid was dissolved in minimal acetone, precipitated into MTBE (1 L), and filtered to afford the title compound (10.0 g, 85%) as a white solid. 1H NMR (500 MHz, (CD3)2CO) delta: 8.66-8.69 (m, 2H), 8.19-8.22 (m, 3H), 8.10-8.13 (m, 4H), 7.91 (d, J=2.5 Hz, 1H), 7.37 (d, J=9 Hz, 1H), 3.96 (s, 3H), 3.61 (s, 2H), 3.57 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 27798-60-3, its application will become more common.

Reference:
Patent; Rohm and Haas Electronic Materials, LLC; LaBeaume, Paul J.; (24 pag.)US9304394; (2016); B2;,
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Adding a certain compound to certain chemical reactions, such as: 5335-05-7, name is Chloromethyl benzoate, 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 5335-05-7, Safety of Chloromethyl benzoate

To a stirred mixture of with NaH (60%, 50 mg, 1.3 mmole) in anhydrous DMF (6 mL) at room temperature under nitrogen was added 2-(6-(4-(2-(tert-butyl-dimethylsilyloxy)ethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, 10 (0.20 g, 0.34 mmole). The resultant mixture was stirred at room temperature for 8 min., then treated with chloromethyl benzoate (0.2 g, 1.2 mmole), the reaction mixture was stirred at room temperature overnight. The reaction mixture was added with aqueous NH4Cl solution and extracted with EtOAc (3×45 mL). The EtOAc solution was washed with 10% LiCl solution and concentrated to an oily residue. The residue was purified by prep. HPLC to give a white solid as impure product and used directly in next step. MS (ESI, M+H+) 736, 738.

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:
Patent; Kim, Kyoung S.; Lee, Francis Y.; Lombardo, Louis J.; Luo, Feng Roger; Wityak, John; US2006/69101; (2006); A1;,
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Synthetic Route of 99548-55-7, 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. 99548-55-7, name is Methyl 4-bromo-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Example 33B Methyl 4-bromo-2-(bromomethyl)benzoate A solution of Example 33A (1.02 g, 4.47 mmol) in CCl4 (22 mL) was treated with AIBN (0.065 g, 0.4 mmol) and NBS (0.955 g, 5.4 mmol), heated to reflux for 4 hours, washed with water, dried (Na2SO4), filtered, and concentrated to provide the desired product (1.1 g, 79%).

The chemical industry reduces the impact on the environment during synthesis Methyl 4-bromo-2-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert; Dinges, Jurgen; Hutchins, Charles; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/187026; (2003); A1;,
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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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: (E)-Ethyl 4-bromobut-2-enoate

General procedure: To a vigorously stirring solution of alpha-imino ester 1 (0.5 mmol,1 equiv) and E-ethyl-4-bromocrotonate or methyl-4-bromocrotonate (2, 1.5 mmol, 3 equiv) in EtOH (2 mL) was added indium powder (1 mmol, 2 equiv). The mixture was allowed to stir vigorously for 6 h at 30 C. After this period, the reaction mixturewas quenched with 2 mL of water and transferred to a separating funnel and extracted using ethyl acetate (315 mL). The combined organic layers were dried over anhydrous Na2SO4. Then the solvent was evaporated under vacuum. Purification of the resulting crude reaction mixture by column chromatography on silica gel (EtOAc/Hexane as eluent) gave the product 3 (see Tables 1 and 2 and Scheme 2 for individual entries).

The synthetic route of 37746-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Aslam, Nayyar Ahmad; Babu, Srinivasarao Arulananda; Sudha, Arya Jayadev; Yasuda, Makoto; Baba, Akio; Tetrahedron; vol. 69; 32; (2013); p. 6598 – 6611;,
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Related Products of 7364-20-7, These common heterocyclic compound, 7364-20-7, name is Methyl 4-ethylbenzoate, 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: (Diacetoxyiodo)benzene (5 mmol, 1.61 g), I2 (0.4 mmol, 102 mg), p-toluenesulfonamide (0.4 mmol, 68.4 mg), and ethylbenzene (2 mmol, 184 mg) were added to dichloroethane (3 mL). The mixture was warmed at 60 C for 2 h under an argon atmosphere. Then, the mixture was poured into saturated aqueous sodium sulfite solution and extracted with diethyl ether (3 × 20 mL). The organic layer was dried over Na2SO4. After filtration and removal of the solvent under reduced pressure, the residue was subjected to preparative TLC on silica gel using a mixture of hexane and ethyl acetate (5:1) as an eluent to give alpha-(acetoxy)ethylbenzene in 63% yield.

Statistics shows that Methyl 4-ethylbenzoate is playing an increasingly important role. we look forward to future research findings about 7364-20-7.

Reference:
Article; Baba, Haruka; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron Letters; vol. 52; 33; (2011); p. 4303 – 4307;,
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These common heterocyclic compound, 1000342-11-9, name is Methyl 3-amino-5-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. Application In Synthesis of Methyl 3-amino-5-bromo-2-methylbenzoate

[01355] Step 4: Synthesis of cis and trans methyl 5-bromo-3-((4-((tert-butoxycarbonyl)amino) cyclohexyl) amino -2-methylbenzoate[01356] To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (5 g, 20.57 mmol) and tert-butyl (4-oxocyclohexyl)carbamate (5.6 g, 26.7 mmol) in methanol (50 mL), acetic acid ( 1 .2 g, 20.57 mmol) was added and reaction stirred at room temperature for 8 h. Then sodium cyanoborohydride (1.6 g, 26.74 mmol) was added at OoC and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography twice eluting with ethyl acetate: hexane to afford (4g , 44%) of less polar cis isomer and (3g, 33%) of the pure more polar trans isomer.

The synthetic route of Methyl 3-amino-5-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
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