Tag: M.W=200-300

Reference of 609-12-1,Some common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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 11.12b: Compound (5-33) KOH, THFZH2Oily-V-33[00438] 3-Methyl-2-(2-methyl~1H-indol-4’yloxy)-butyric acid ethyl ester (2): A mixture of 4-hydroxy-2-methylindoie (1) (1.5 g, 0.010 mole), 2-bromo-3-methyl-butyric acid ethyl ester (2.2 g, 0.010 mole) and potassium carbonate (excess) in acetone (50 mL) was refluxed for 3 days. The reaction mixture was filtered, and the filtrate was concentrated. The residue was purified by column chromatography (20:1 Hex:EtOAc) to afford intermediate 2. Yield: 1.88 g, 71 %

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2-bromo-3-methylbutanoate, its application will become more common.

Reference:
Patent; ILYPSA, INC.; WO2007/56279; (2007); A2;,
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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. 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 2-(3-bromophenyl)acetate

Step B:; To a solution of (3-bromophenyl) -acetic acid methyl ester 46 (1.20 g, 5.28 mmol) in dry dimethyl-acetamide (5 mL) is added under argon zinc cyanide (0.78 g, 6.64 mmol) and tetrakis(triphenylphosphine) palladium (0.63 g, 0.55 mmol). The mixture is stirred for 24 hours at 80C. After cooling to room temperature, the mixture is diluted with EtOAc (15 mL) and water (20 mL). The resulting precipitate is removed by vacuum filtration. The organic layer of the filtrate is separated and washed with H20, then dried over MgS04, filtered and concentrated. Purification by silica gel chromatography (0 to 20% EtOAc/hexane) to give (3-cyano-phenyl) acetic acid methyl ester 47 as an oil: ¹H-NMR (400MHz, CDCl3) 8 = 7.63 (d, J= 8.0 Hz, 1H), 7.47 (d, J= 1.2 Hz, 1H), 7.30 (dd, J= 1.2 Hz, J= 8.0 Hz, 1H), 3.72 (s, 3H), 3.69 (s, 2H). MS calculated for C10H9O2ClN (M+W) 210.0, found 210.0.

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 150529-73-0.

Reference:
Patent; IRM LLC; WO2005/113519; (2005); A1;,
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Synthetic Route of 110661-91-1,Some common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, molecular formula is C8H15BrO2, 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.

This was prepared as per 25e from 24 using t-butyl 4-bromobutanoate. Yield 21%. 1H NMR (300 MHz, CHLOROFORM-d) d7.18-7.33 (m, 3H), 7.09 (d,J= 6.78 Hz, 2H), 6.98 (br s, 1H), 6.87 (d,J= 8.29 Hz, 1H), 6.65-6.73 (m, 2H), 6.58-6.64 (m, 1H), 6.46 (dd,J= 2.17, 8.19 Hz, 1H), 6.33 (d,J= 2.07 Hz, 1H), 4.47 (dd,J= 8.01,14.98 Hz, 1H), 3.79 (s, 3H), 3.73 (s, 3H), 3.54-3.69 (m, 2H), 3.32-3.47 (m, 1H), 3.14 (t,J= 6.88 Hz, 2H), 3.07-3.32 (m, 2H), 2.76-2.99(m, 4H), 2.41-2.54 (m, 1H), 2.34 (t, J= 7.16 Hz, 2H), 1.90 (quin,J= 7.02 Hz, 2H), 1.46 (s, 9H).m/z588 (M+H)

The synthetic route of 110661-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Perrey, David A.; Decker, Ann M.; Li, Jun-Xu; Gilmour, Brian P.; Thomas, Brian F.; Harris, Danni L.; Runyon, Scott P.; Zhang, Yanan; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5709 – 5724;,
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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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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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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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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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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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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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Related Products of 72594-86-6,Some common heterocyclic compound, 72594-86-6, name is Benzyl tert-butyl malonate, molecular formula is C14H18O4, 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 5 2-(2-Methylthioethyl)propenoic acid benzyl ester Sodium hydride (0.96 g, 50percent suspension in mineral oil) was added to a stirred solution of t-butyl benzyl malonate (5 g) in dry dimethylformamide (50 ml), maintained at 0°C under an atmosphere of nitrogen. After stirring for 15 minutes, 2-chloroethyl-methyl sulphide (2.21 g) in dimethylformamide (10 ml) was added dropwise, while the temperature of the reaction was maintained below 10°C. The reaction was allowed to warm to room temperature and stirred for 15 hours when water was cautiously added. The reaction mixture was extracted with ethyl acetate (2 x 100 ml), the ethyl acetate extracts were washed with water (4x), dried (Na2SO4) and evaporated to give 4-methylthio-2-t-butyloxycarbonyl-butanoic acid benzyl ester as an oil (6.4 g).

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

Reference:
Patent; Pfizer Limited; EP274234; (1991); B1;,
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