Month: July 2021

These common heterocyclic compound, 24398-88-7, name is Ethyl 3-bromobenzoate, 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. Formula: C9H9BrO2

Method A; Step e: 1-(3-bromophenyl)-2-pyridin-4-ylethanone; To 66 ml (0.066 mol) of sodium 1,1,1,3,3,3-hexamethyldisilazane 1M in THF under nitrogen atmosphere at 00C, 3.2 ml (0.033 mol) of 4-picoline were added. After stirring for 60 minutes 5 ml (7.15 g; 0.03 mol) of ethyl 3-bromo benzoate were added and the mixture maintained in the same conditions for 1.5 hours. HCI 2N was then added, the mixture made basic with NaOH 2N and extracted with ethyl acetate. The organic phase was dried over Na?SCM and the solvent evaporated. 7.5 g (82% yield) of the title compound were obtained by crystallization from AcOEt-Et2U. 1H NMR (401 MHz, DMSO-d6) delta = 8.52 (d, J = 6.0 Hz, 2 H), 8.19 (t, J = 1.7 Hz, 1 H), 8.05 (ddd, J = 1.0, 1.6, 7.8 Hz, 1 H), 7.89 (ddd, J = 1.0, 2.0, 8.0 Hz, 1 H), 7.54 (t, J = 7.9 Hz, 1 H), 7.19 – 7.33 (m, 2 H), 4.53 (s, 2 H). MS-ESI (M+H) calc. 276.0019 found 276.0023 (C13HIOBrNO)

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

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; PULICI, Maurizio; ZUCCOTTO, Fabio; BADARI, Alessandra; NUVOLONI, Stefano; CERVI, Giovanni; TRAQUANDI, Gabriella; BIONDARO, Sonia; TRIFIRO’, Paolo; MARCHIONNI, Chiara; MODUGNO, Michele; WO2010/10154; (2010); 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. 5616-81-9, name is tert-Butyl 2-(methylamino)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of tert-Butyl 2-(methylamino)acetate

A mixture of 2-chloromethyl-8-nitropyridine, (10 mmol), sarcosine t-butyl ester (11 mmol) and finely ground anhydrous potassium carbonate (30 mmol) in ethylene glycol dimethyl ether (DME) (20 mL) is heated under reflux for 8 hours. The reaction mixture is filtered hot and solid is washed with 30 mL of DME. The filtrate is evaporated in vacuo and the crude product is purified by recrystallization or chromatography to give 2-(N-methyl-N-t-butoxycarbonylmethyl)methyl-8-nitroquinoline.

The synthetic route of 5616-81-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bioflexis, LLC; US2006/94755; (2006); A1;,
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Reference 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.

General procedure: 1.4mmol of 5-amino-1-substituted-4-carboxamide-1H-imidazole (1) was dissolved in 10mL of absolute methanol. Then 5.6mmol of the appropriate ester isadded into this solution. This mixture was added in 10mL ofmethoxide-methanol solution prepared from sodium (0.15 g, 6.3mmol) and 10mL of absolute methanol. The mixture was refluxed for 15-20 h. After cooling, the solvent was evaporated off and the residue was taken into ethyl acetate. The organic phase was dried over Na2SO4 and evaporated. And the residue was purified via silica gel chromatography(eluent: the mixture of ethyl acetate and methanol) to obtainthe pure product (2a-2q).

The synthetic route of 15964-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yuan, Wei; Zhao, Xin-Yun; Chen, Xi; Zhan, Chang-Guo; Journal of Chemistry; vol. 2016; (2016);,
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Electric Literature of 90942-47-5, A common heterocyclic compound, 90942-47-5, name is Methyl 5-(aminomethyl)-2-chlorobenzoate hydrochloride, molecular formula is C9H11Cl2NO2, 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 solution of methyl 5-(aminomethyl)-2-chlorobenzoate hydrochloride (1.80 g, 6.00 mmol) in THF (20 mL) were added DIPEA (3.096 g, 24.0 mmol) and pivaloyl chloride (1.2 mL, 9.0 mmol). The reaction mass was stirred at rt for 2 h, diluted with EtOAc and was washed with water, and brine. The organic layer was separated, dried, filtered and concentrated to afford 2.0 g of the title product. 1H NMR (300 MHz, DMSO-i): delta 8.16 (m, 1H), 7.65 (s, 1H), 7.53 (d, J = 8.4 Hz, 1H), 7.41 (d, J = 8.4 Hz, 1H), 4.25 (d, J = 5.7 Hz, 2H), 3.85 (s, 3H), 1.15 (s, 9H).

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; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; BANERJEE, Abhisek; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2014/167444; (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. 17994-94-4, name is Methyl 7-aminoheptanoate hydrochloride belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Methyl 7-aminoheptanoate hydrochloride

Methyl 7-(4-(2-oxo-2-(quinolin-8-ylamino)ethyl)benzamido)heptarioate, 69.; Compound 68 (200 mg, 0.65 mmol) was dissolved in CH2CI2 (20 mL) under argon. To this added 7-aminoheptanoic acid methyl ester (as the hydrochloride, 140 mg, 0.72 mmol), Et3N (73 mg, 0.72 mmol) and EDC (138 mg, 0.72 mmol) and the mixture was allowed to stir overnight at it. Added water and worked up with CH2CI2, the residue purified through flash column (silica gel 230-400 mesh, 80% ethyl acetate in hexanes) to ohtain 69 as white solid (238 mg, 82%). NMR (400 MHz, CDC13): S = 1.35-1.37 (m, 4 H), 1.58-1.64 (m, 4 H), 2.29 (t, 2 , J = 7.2 Hz), 3.43 (q, 2 H, J = 6.8 Hz), 3.64 (s, 3 H), 3.92 (s, 2 H), 6.18 (s, 1 H), 7.41-7.51 (m, 5 H), 7.77 (d, 2 H, J = 8 Hz), 8.15 (d, 1 H, J = 8 Hz), 8.71-8.73 (m, 2 H), 9.95 (s, 1 H). I3C NMR (75 MHz, CDC13): delta = 24.7, 26.5, 28.6, 33.8, 39.9, 44.7, 51.3, 116.3, 121.6, 121.8, 127.0, 127.6, 127.7, 129.4, 133.7, 134.0, 136.2, 137.9, 138.1, 148.2, 167.3, 168.9, 174.1 LRMS Calcd for C26H29N3O4: 448.21 Found: 447.90.

The synthetic route of 17994-94-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; BRESLOW, Ronald; MARKS, Paul, A.; ABHILASH, K., G.; WANG, Jianing; WO2011/146855; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, 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 69812-51-7, Quality Control of Methyl 4-chlorosulfonylbenzoate

Example 5-10b Methyl 4-(N-(4-methoxybenzyl)sulfamoyl)benzoate To a solution of methyl 4-(chlorosulfonyl)benzoate (Example 5-10c) (4 g, 17.09 mmol) in dichloromethane (40 mL) at 0 C. in an ice bath, was added (4-methoxyphenyl)methanamine (2.56 mL, 19.65 mmol) and triethylamine (2.38 mL, 17.1 mmol). The ice bath was then removed and the mixture was allowed to warm to ambient temperature with stirring for an additional 2 hours. Upon completion (monitored by TLC 40% ethyl acetate/hexanes), the solvent was removed in vacuo. The residue was re-dissolved in ethyl acetate (200 mL), washed with 1N HCl (aq, 20 mL), water (20 mL) and brine (20 mL) then dried over magnesium sulfate. The solution was concentrated and the product purified by re-crystallization with hot ethyl acetate/hexanes to afford pure methyl 4-(N-(4-methoxybenzyl)sulfamoyl)benzoate (4.3 g, 74.8%) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta, ppm: 3.67 (s, 3H), 3.78 (s, 3H), 3.93 (s, 2H), 6.78 (m, 2H), 7.09 (m, 2H), 7.87 (m, 2H), 8.08 (m, 2H), 8.25 (br, s, 1H).

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; Senomyx, Inc.; US2009/274632; (2009); A1;,
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Reference of 82702-31-6, 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. 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

12a In accordance with a method known from the literature, methyl 3-bromo-4-fluorobenzoate is reacted, under (Ph3 P)2 PdCl2 catalysis, with (trimethylsilyl)acetylene to form methyl 4-fluoro-3-(2-trimethylsilylethinyl)benzoate. MS (ES): 251 (M+1).

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 3-bromo-4-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoechst Aktiengesellschaft; US5679712; (1997); A;,
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Application of 23426-63-3, The chemical industry reduces the impact on the environment during synthesis 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, I believe this compound will play a more active role in future production and life.

Example 12A Methyl-3,3-dicyano-2,2-dimethylpropanoate In THF (91 ml), 3 g (45.411 mmol) of malonic acid dinitrile was slowly added to 1.816 g (45.411 mmol) of sodium hydride (60% in mineral oil). Then 5.876 ml (45.411 mmol) of methyl-2-bromo-2-methylpropanoate was added and it was stirred overnight at RT. Then a further 5.876 ml (45.411 mmol) of methyl-2-bromo-2-methylpropanoate was added and it was heated overnight to 50 C. Then once again, 1.762 ml (13.623 mmol) of methyl-2-bromo-2-methylpropanoate was added and it was heated for a further 4 h to 50 C. Saturated aqueous sodium hydrogen carbonate solution was then added to the mixture and it was extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and evaporated to dryness. 8.9 g of raw product was obtained, and was purified by silica gel chromatography (cyclohexane-ethyl acetate 4:1). Yield: 6.47 g (85% of theor.) 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.40 (s, 6H), 3.74 (s, 3H), 5.27 (s, 1H).

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-bromo-2-methylpropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; FOLLMANN, Markus; STASCH, Johannes-Peter; REDLICH, Gorden; GRIEBENOW, Nils; LANG, Dieter; WUNDER, Frank; HUeBSCH, Walter; LINDNER, Niels; VAKALOPOULOS, Alexandros; TERSTEEGEN, Adrian; US2013/338137; (2013); 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. 207346-42-7, name is Methyl 2-amino-4,5-difluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H7F2NO2

Methyl 2-amino-4,5-difluorobenzoate (14) (250 mg, 1.33 mmol) was dissolved in 4mL DMF. TEA (2.5 eq) and R-tert-butyl(pyrrolidin-3-yl methyl) carbamate (298.5 mg, 1.47 mmol) were added and stirred at 80 C for 5 h. The reaction mixture was dissolved in 20 mLDCM and washed with 10 mL water three times. The organic layer was concentrated by rotary evaporation. The residual DMF was removed by placing under high vacuum overnight. The residue was purified by silica gel chromatography using gradient from 3:1Hexanes:EtOAc to 1:1 Hexanes:EtOAc to yield pure UICK-II-189(15) Yield 73%. 1H NMR (300 MHz, CDCl3) d 7.43 (d, J 15.4 Hz,1H), 5.73 (d, J 7.8 Hz, 1H), 4.70 (bs, 1H, exchangeable), 3.82 (s, 3H),3.53 (m, 3H), 3.20 (m, 3H), 2.47 (m, 1H), 2.08 (m, 1H), 1.71 (m, 1H),1.47 (s, 9H). 19F NMR (282 MHz, CDCl3) d 141.00 (s, 1F). MS (ESI) calculated for (M H) 368.19, found 368.0.

According to the analysis of related databases, 207346-42-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Delgado, Justine L.; Lentz, Sarah R.C.; Kulkarni, Chaitanya A.; Chheda, Pratik R.; Held, Hailey A.; Hiasa, Hiroshi; Kerns, Robert J.; European Journal of Medicinal Chemistry; vol. 172; (2019); p. 109 – 130;,
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Reference of 57486-69-8, 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. 57486-69-8, name is Methyl 2-(2-bromophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of methyl 2-(2-(pyridin-4-yl)pIn a sealed degassed vial, methyl-2-(2-bromophenyl)acetate (550 mg, 2.4 mmol), 4-pyridine boronic acid (325 mg, 2.64 mmol), 2 M Na2C03 (4 mL), DME (8 mL), Pd(PPh3)4 (140 mg, 0.12 mmol) was combined. The vial was charged with argon and then placed in the microwave reactor, heating at 120 C for 20 minutes. Reaction was diluted with 10 mL of EtOAc and then washed with brine. The mixture was dried with MgS04 and then by reduced pressure. The title compound was obtained after purification by flash chromatography (100% hexanes to 50% EtOAc/hexanes): yellow oil (330 mg, 60%). MS ESI [M + H]+ 228.0, calcd for [Ci4H,3N02 + H]+ 228.1

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-bromophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; LAUFER, Radoslaw; PAULS, Heinz W.; FEHER, Miklos; NG, Grace; LIU, Yong; EDWARDS, Louise G.; PATEL, Narendra Kumar B.; PAN, Guohua; MAK, Tak W.; WO2011/123937; (2011); A1;,
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