Month: May 2021

Electric Literature of 27741-65-7, These common heterocyclic compound, 27741-65-7, name is Ethyl 2-cyclobutylideneacetate, 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.

In 1:1:0.5 THF/water/Methanol (10:10:5 mL each), ethyl 2-cyclobutylideneacetate (1.2 g, 8.57 mmol) and lithium hydroxide monohydrate (2.15 g, 51.4 mmol) was added at room temperature. Reaction mixture was allowed to stir at room temperature for 16 h. TLC showed absence of starting material (Rf=0.4, 30% ethyl acetate/n-hexane). THF and Methanol was removed under reduced pressure. Aqueous layer was acidified with citric acid and extracted with ethyl acetate. Crude product was purified by column chromatography (silica gel 60-120 mesh ethyl acetate/n-hexane as eluent) to afford white solid. [0505] Yield: 0.6 g (62%) [0506] 1H NMR (400 MHz, CDCl3): delta 2.02-2.20 (m, 2H). 2.86 (t, J=7.8 Hz, 2H), 3.14 (t, J=7.8 Hz, 2H), 5.59 (t, J=2 Hz, 1H).

Statistics shows that Ethyl 2-cyclobutylideneacetate is playing an increasingly important role. we look forward to future research findings about 27741-65-7.

Reference:
Patent; Cornell University; Coferon, Inc.; Purdue Research Foundation; Barany, Francis; Pingle, Maneesh; Bergstrom, Donald E.; Giardina, Sarah F.; Arnold, Lee Daniel; US2014/194383; (2014); A1;,
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Electric Literature of 144851-82-1,Some common heterocyclic compound, 144851-82-1, name is Methyl 2-amino-3-fluorobenzoate, molecular formula is C8H8FNO2, 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 suspension of methyl triphenylphosphonium bromide (2.4 eq) and sodium amide (3.2 eq) in toluene (0.1 M) was stirred at RT for 3 h. After cooling down to 00C, a solution of Dl in toluene (0.1 M) was added to the suspension and the reaction mixture was heated to 500C for 3 h. 30 min. Then, The precipitate was filtered off and the solvent was evaporated under reduced pressure giving a crude that was purified by flash chromatography on silicagel, using AcOEt/PE (7:3) as solvent, affording the title compound as a yellow powder.1U NMR (500 MHz, CDCl3) delta: 7.78-7.68 (m, 6H), 7.62-7.54 (m, 3H), 7.52-7.45 (m, 7H), 6.97-6.89 (m, IH), 6.56-6.48 (m, IH), 5.76 (bs, 2H), 4.32-4.20 (m, IH). MS (ES) C26H2iFNOP requires: 413, found: 414 (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-amino-3-fluorobenzoate, its application will become more common.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2009/27730; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 457097-93-7, name is Methyl 4-amino-3-(trifluoromethoxy)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 457097-93-7

[Step 1] 4-[(Methylsulfonyl)amino]-3-(trifluoromethoxy)benzoic acid To a solution of methyl 4-amino-3-(trifluoromethoxy)benzoate (600 mg) in chloroform (20 ml), triethylamine (2.12 ml) and methanesulfonyl chloride (0.795 ml) were added dropwise under ice-cooling. The reaction solution was stirred at 0 C. for 10 minutes and at room temperature for 2 hours. Saturated sodium bicarbonate water was added thereto, and the reaction solution was stirred at room temperature for 20 minutes and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was dissolved in methanol (20 ml). A 1 N aqueous solution of sodium hydroxide (20.4 ml) was added and the resultant reaction solution was stirred at 70 C. for one hour while heating. After the temperature of the solution was returned to room temperature and the reaction solution was concentrated up to about half under reduced pressure, 5 N hydrochloric acid (4 ml) was added dropwise. The precipitated solid was collected by filtration and dried under reduced pressure to obtain the title compound (740 mg) as a solid. 1H-NMR (DMSO-D6) delta: 3.17 (3H, s), 7.70 (1H, d, J=8.5 Hz), 7.81-7.84 (1H, m), 7.93 (1H, dd, J=8.9, 2.1 Hz), 10.25 (1H, s), 13.31 (1H, s). MS (ESI/APCI) m/z: 298 [M-1]-

The synthetic route of 457097-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; Ota, Masahiro; Inoue, Hidekazu; Kawai, Junya; Ohki, Hitoshi; Toki, Tadashi; (25 pag.)US2019/284198; (2019); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, A new synthetic method of this compound is introduced below., COA of Formula: C9H11NO2

In a 10 mL pear-shaped flask, 6,7-dimethoxy-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylic acid (92.0 mg, 0.366 mmol, 1.00 eq) (from Example 71, Step D supra) and methyl 3-amino-4-methylbenzoate (90.7 mg, 0.549 mmol, 1.50 eq) (TCI) were combined in DMF (1.1 mL). Triethylamine (0.255 mL, 1.83 mmol, 5.00 eq) and then HATU (209 mg, 0.540 mmol, 1.50 eq) (Aldrich) were added resulting in a yellow solution. After stirring for 3 hours at room temperature the reaction was diluted with EtOAc, extracted twice with water and once with brine and then concentrated. The solid residue was triturated with water and then with hot EtOAc to give 3-[(6,7-dimethoxy-2-oxo-1,2,3,4-tetrahydro-quinoline-3-carbonyl)-amino]-4-methyl-benzoic acid methyl ester. (Yield 97.2 mg, 0.244 mmol, 66.6%). HR-MS (ES+) m/z Calculated for C21H22N2NaO6 ([M+Na]+): 421.1370. Found: 421.1371.

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; Dominique, Romyr; Luk, Kin-Chun; Qiao, Qi; Rossman, Pamela Loreen; US2012/184548; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 206551-41-9, These common heterocyclic compound, 206551-41-9, name is Methyl 3-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.

Example 198 3-Bromo-2[-(4-methoxybenzenesulfonyl)amino]-benzoic acid methyl ester To 0.096g (0.5 mmol) of 4-methoxyphenylsulphonamide in 3mL of DMF was added in one portion 0.020g (0.50 mmol) of 60percent sodium hydride and the reaction was stirred at 25-C for 15 min. Then, 0.135g (0.58 mmol) of methyl 3-bromo-2-fluorobenzylate was added to the solution in one portion and the resulting mixture was heated at 90 ¡ãC (bath temperature) for 18h. The reaction was cooled to room temperature, acidified with 1N HCl and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica eluding with 30percent-50percent ethyl acetate/hexane to provide 0.037g (19percent) of the desired product. 1H-NMR(CDCl3): 8 ppm (s, 1H, NH), 6.8-7.8 ppm (m, 7H, Ar), 3.9 ppm (s, 1H, OMe), 3.7 ppm (s, 1H, OMe).

The synthetic route of 206551-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; EP938471; (2001); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 6091-64-1, These common heterocyclic compound, 6091-64-1, name is Ethyl 2-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.

To a tube was added Hphosphinate 3a (173 mg, 1 mmol, 1 equiv), Pd(OAc)2 (4.5 mg, 0.02 mmol, 2 mol %), xantphos (12.7 mg, 0.022 mmol, 2.2 mol %), toluene and 1,2-dimethoxyethane (4.5 ml : 0.5 ml), i-Pr2NEt (0.23 ml, 1.3 mmol, 1.3 equiv) and ethyl-2-bromobenzoate (0.24 mL, 1.5 mmol, 1.5 equiv). The homogeneous mixture was stirred under a flow of N2 for 10 minutes and then heated at 115C for 24 hrs. The solvent was then evaporated and the resulting residue partitioned between EtOAc (10 ml) and NaHCO3 (5 ml). The aqueous layer was extracted with EtOAc (3x). The organic layers were combined, dried over MgSO4 and concentrated under reduced pressure. The resulting oil was then purified by chromatography (silica gel, hexane/ EtOAc, 5:5) to give a yellow oil. Yield: 83% (232 mg); 1H NMR (CDCl3, 300 MHz) delta 8.04-8.11 (m, 1H), 7-77-7.81 (m, 1H), 7.59-7.64 (m, 2H), 4.41 (q, J = 7.0 Hz, 2H), 3.75-4.07 (dm, 2H), 1.90 (d, J = 15.2 Hz, 3H), 1.60-1.67 (m, 2H), 1.35-1.47 (m, 5H), 0.92 (t, J = 7.3 Hz, 3H) ppm; 13C NMR (CDCl3, 75.45 MHz) delta 168.1 (d, JPCCC = 3.4 Hz), 135.9 (d, JPCCC = 7.8 Hz), 133.9 (d, JPCCC = 8.1 Hz), 132.0 (d, JPCCCC = 2.3 Hz), 131.6 (d, JPC = 120.6 Hz), 131.0 (d, JPCC = 11.5 Hz), 129.7 (d, JPCC = 9.8 Hz), 64.5 (d, JPOC = 6.3 Hz), 61.9, 32.6 (d, JPOCC = 6.6 Hz), 18.9, 17.3 (d, JPC = 103.9 Hz), 14.2, 13.7 ppm; 31P NMR (CDCl3, 121.47 MHz) delta 43.07 ppm; HRMS (EI+) calcd for C14H21O4P 284.1177, found 284.1179.

Statistics shows that Ethyl 2-bromobenzoate is playing an increasingly important role. we look forward to future research findings about 6091-64-1.

Reference:
Article; Gavara, Laurent; Petit, Christelle; Montchamp, Jean-Luc; Tetrahedron Letters; vol. 53; 37; (2012); p. 5000 – 5003;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 41658-03-1, name is Ethyl 3-bromopropiolate, 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 41658-03-1, COA of Formula: C5H5BrO2

General procedure: A solution of 3-phenyl sydnone (3, 100 mg, 1.0 equiv) in 4.0 mL p-xylene was added ethyl 3-bromopropynoate (120 mg, 1.05 equiv) and heated to reflux for 5 h. The residue was cooled down and added 2-aminophenylboronic acid pinacol ester (820 mg, 1.1 equiv), Pd(PPh3)4 (39 mg, 0.1 equiv), K2CO3 (2 mL, 2 M aqueous solution), and EtOH (4.0 mL). The reaction mixture was stirred at reflux for 24 h. When the reaction was completed, the reaction mixture was concentrated under reduced pressure to remove p-xylene and EtOH. The residue was added with 20 mL water, and extract with EtOAc (40 mL). The organic layer was filtered to remove the insoluble substances, then dried over MgSO4, filtered, and concentrated under reduced pressure. The residue solution was purified by column chromatography on silica gel to give the corresponding 2-arylpyrazolo[3,4-c]quinolin-4(5H)-one 1b-e and 2-arylpyrazolo[4,3-c]quinolin-4(5H)-one 2b-e products in 27-32% and 39-43% yields, respectively.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-bromopropiolate, and friends who are interested can also refer to it.

Reference:
Article; Chang, En-Chiuan; Wen, Ya-Lan; Chang, Chun-Hsi; Shen, Yun-Hwei; Wen, Shaw-Bing; Yeh, Mou-Yung; Wong, Fung Fuh; Tetrahedron; vol. 68; 29; (2012); p. 5920 – 5924;,
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Ester – an overview | ScienceDirect Topics

Electric Literature of 142-91-6, 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. 142-91-6, name is Isopropyl palmitate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1.41 g of isopropyl palmitate (manufactured by Wako Pure Chemical Industries Ltd.), 1.00 g of phytosphingosine,and 14 mL of ethanol were added in a 30-mL eggplant flask and the mixture was stirred in a 55C hot water bath for 15min. After it was confirmed that the reaction system was homogeneous, 17.7 mg of potassium hydroxide (manufacturedby Kanto Chemical Co. , Inc.) was added. After 2 hours, a precipitate was confirmed and the mixture was continuouslystirred during a whole day and night. After the resulting reaction mixture was cooled to 30C, the precipitate was filteredand washed to obtain 1.45 g of N-hexadecanoyl-phytosphingosine in the form of a white solid in a yield of 82.9% (purity:95%).Melting point 114-117CIR (ATR, cm-1) 3336, 2917, 2849, 1611, 1542, 1468, 1076, 717MS (positive): [M + H]+ = 556.7, [M + Na]+ = 584.71H-NMR (deuterated pyridine, 500MHz, delta) 0.85 (3H, t, J = 7.0Hz), 0.85 (3H, t, J = 7.0Hz), 1.16-1.49 (46H, br), 1.69 (1H,m), 1.82 (2H, m), 1.94(2H, m), 2.24 (1H, m), 2.45 (2H, t, J = 7.6Hz), 4.29 (1H, m), 4.40 (1H, ddd, J = 5.9, 5.9, 5.5Hz),4.49 (2H, m), 5.10 (1H, m), 6.19 (1H, d, J = 6.7Hz), 6.53 (1H, d, J=6.2Hz), 6.62 (1H, t, J=5.4Hz), 8.52 (1H, d, J=8.5Hz)

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, Isopropyl palmitate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kao Corporation; HASHIMOTO, Hiroshi; SUGAI, Yoshiya; EP2757090; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 18013-97-3, 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. 18013-97-3, name is Diethyl 2,5-dibromoterephthalate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2,5-Dibromo-terephthalic acid diethyl ester (20 g, 53 mmol), dibenzofuran- 1 -boronic acid (29 g, 137 mmol) and tripotassiumphosphate monohydrate (48.5 g, 160 mmol) were added to water/toluene/dioxane (1 :1 :1 , 0.5 L). The solution was saturated with argon. Palladium(ll)-acetate (1 18 mg, 0.5 mmol) and tri-o-tolyl-phosphine (480 mg, 1 .6 mmol) were added and the reaction mixture was refluxed for 16 hours. After cooling down to room temperature, toluene (500 mL) was added and the organic phase was washed with water (3 x 500 mL) and then concentrated under reduced pressure. The residue was purified by recrystallization from toluene/ethanol. Yield: 22.2 g (40 mol; 76 %).

The synthetic route of Diethyl 2,5-dibromoterephthalate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; LINGE, Rouven; RODRIGUEZ, Lara-Isabel; MEYER, Sebastian; HEIL, Holger; (112 pag.)WO2018/95888; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 14062-24-9, These common heterocyclic compound, 14062-24-9, name is Ethyl 4-chlorophenylacetate, 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: Sodium hydride (1.33 ml, 2.61 mmol) was added dropwise to a solution of phenyl acetonitrile (1.0 g, 8.5 mmol)) in anhydrous THF (30 mL), the mixture was stirred at R.T. for30 minutes, followed by adding a solution of ethyl 4-chlorobenzoate (1.78 g, 10.2 mmol) in anhydrous THF (30mL). The mixture was refluxed till the reaction was finished.The result mixture was quenched with water and extracted with ether. The aqueous layer was acidified with 10% HCl to filter out the white precipitation, which was recrystallized with ether to give a white solid. Yield: 76%-80%.

The synthetic route of 14062-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hu, Chunqi; Shen, Jianfeng; Du, Wenting; Letters in drug design and discovery; vol. 14; 2; (2017); p. 151 – 158;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics