Author: Jessica.F

Application of 174579-31-8, These common heterocyclic compound, 174579-31-8, name is tert-Butyl 2-(4-aminophenyl)acetate, 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.

Synthesis of compound 2.6. A solution of compound 2.5 (1.0 g, 3.19 mmol, 1.0 eq), tert-butyl 2-(4-aminophenyl)acetate (0.661g, 3.19 mmol, 1.00 eq) and K2C03 (1.32 g, 9.57 mmol, 3.0 eq) in DMF (10.0 mL) was heated at 90 C for 12 hours. Upon completion, the mixture was cooled to room temperature and poured into water. The product was extracted with ethyl acetate (50mL X 3). And the combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified using flash column chromatography to afford the compound 2.6 (1.10g, 71.4%) MS (ES): m/z 484.2 [M+H]+.

The synthetic route of 174579-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
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Related Products of 136333-97-6,Some common heterocyclic compound, 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, molecular formula is C10H11BrO2, 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 11A Diallyl 2-[4-(methoxycarbonyl)benzyl]-2-{2-[4-(methoxycarbonyl)phenyl}ethyl]malonate At room temperature, 62.66 g (192 mmol) of cesium carbonate and 46.75 g (154 mmol) of methyl 4-(2-bromoethyl)benzoate [CAS Reg. No. 136333-97-6] are added to a solution of 42.61 g (128 mmol) of diallyl 2-(4-methoxycarbonylbenzyl)malonate in 450 ml of DMF. The mixture is then stirred at room temperature overnight. After the reaction has gone to completion, the reaction solution is evaporated to dryness, and the residue is taken up in water and extracted three times with ethyl acetate. The combined organic phases are then washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is removed to dryness under reduced pressure. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 13:1). This gives 41.35 g (83.6 mmol, 65% of theory) of a colorless solid. LC-MS (Method 2): Rt=2.92 min; m/z=495 (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 4-(2-bromoethyl)benzoate, its application will become more common.

Reference:
Patent; Hahn, Michael; Becker, Eva-Maria; Knorr, Andreas; Schneider, Dirk; Stasch, Johannes-Peter; Schlemmer, Karl-Heinz; Wunder, Frank; Lang, Dieter; US2010/197680; (2010); A1;,
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Synthetic Route of 3618-04-0, These common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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.

PREPARATION 1: 1 – Allyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarbaldehyde; Step a: 4-(/ert-Butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester:; [00160] To a 50 mL flask was added 4-hydroxy-cyclohexanecarboxylic acid ethyl ester (5.0 g; 29.0 mmol), imidazole (2.37 g; 34.8 mmol), DMF (30 mL) and ter/-buryldimethylsilyl chloride (4.81 g; 32.0 mmol). The solution was stirred for 78h at 20 0C. The reaction was diluted with EtOAc (100 mL), washed with water 2 x 100 mL), brine (100 mL), dried (MgSO4) filtered and concentrated in vacuo. The crude oil was purified by flash chromatography (silica gel, hexanes/EtOAc 1:0 to 1:1) to give pure product (7.79 g, 94% yield) as a 2:1 mixture of diastereomers.1H-NMR (400 MHz, CDCl3) (J = Hz) delta mixture 4.12 (m; 2H), 3.90 (m; 0.65H), 3.58 (m; 0.35H), 2.23 (m; IH), 1.98 (m; 3H), 1.82 (m; 3H), 1.49 (m; 2H), 1.21 (m; 3H), 0.88 (s; 9H), 0.05 (s; 3H), 0.03 (s; 3H). 13C-NMR (400 MHz, CDCl3) delta mixture 175.7, 175.6, 70.5, 66.6, 60.1, 60.0, 42.2, 42.1, 34.8, 32.8, 27.2, 25.8, 25.6, 23.4, 18.2, 18.0, 14.2, -4.7, -4.9. MS (ES+) m/z 287.22 [MH+].

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN IDEC MA INC; WO2007/76086; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 52787-14-1, name is Methyl 4-(2-methoxy-2-oxoethyl)benzoate, A new synthetic method of this compound is introduced below., Computed Properties of C11H12O4

Under argon protection, 323g of PLQS-1 and 2.26L of THF were added to a 5L three-necked flask. When the temperature was lowered to -10C, 224ml of 3-bromopropyne was poured into the reaction flask, and the temperature was stirred for 0.5h to start dropping. 1.8L 1mol/L. LiHMDS solution in THF, control the dropping rate, and keep the reaction temperature at -10±3C (about 2~3h). After completion of the addition, stirring was continued for 0.5 h. HPLC detection was completed. After the reaction was completed, the reaction solution was poured into 1.25 L of acetic acid aqueous solution, stirred for 10 minutes, and then liquid-separated. The organic phase was concentrated under reduced pressure at 50 C. to remove the solvent, and the solution was concentrated. About 1.3L of isopropanol was added, and the precipitated solid was stirred and put into 0 to 5C.Cold bathThe mixture was stirred for 3 to 4 hours, filtered, and the filter cake was washed with about 300 ml of a mixed solvent of isopropanol:n-heptane = 1:6. The filter cake was dried in an oven at 50 C. to give 332 g of a pale yellow solid with a yield of 87.0%. The intermediate alpha-propargyl-(4-Methyl formate)-methyl phenylacetate (PLQS-2)The HPLC assay content is 99.6%.The HPLC content of the dipropargyl substituent was 0.3%.

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; Shandong New Age Pharmaceutical Co., Ltd.; Zhang Guimin; Chen Chengfu; Wei Chuanbing; (7 pag.)CN107488112; (2017); A;,
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Application of 706791-83-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 706791-83-5 name is Methyl 3-amino-5-bromobenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of methyl 3-amino-5-bromobenzoate (61b, 219 mg, 0.950 mmol) in 1,4-dioxane (20 mL) were added bis(pinacolato)diboron (290 mg, 1.14 mmol), PdCl2(dppf) (23 mg, 28.5 pmol) and potassium acetate (279 mg, 2.85 mmol), and then this reaction mixture was stirred at 95 C for 15 h. The reaction mixture was partitioned ethyl acetate (20 mL) and water (10 mL), and the aqueous layer was extracted with ethyl acetate (10 mL x 2). The combined organic layer was washed brine (5 mL), dried over MgS04, filtered and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4: l) to afford compound 62 (180 mg, 68%) as a white solid; NMR (400 MHz, CDC13) d 7.88 (s, 1H), 7.46 (s, 1H), 7.31 (d, J =2.4 Hz, 1H), 3.91 (s, 3H), 1.36 (s, 12H); MS (ESI, m/z) 278.2 [M+l]+; ESI-HRMS calcd. m/z for (0572) Ci4H2iN04nB 278.1564, found 278.1565 [M+l]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-5-bromobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; JACOBSON, Kenneth A.; YU, Jinha; CIANCETTA, Antonella; WEN, Zhiwei; JUNG, Young-Hwan; (124 pag.)WO2019/157417; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common compound: 1559-02-0, name is Diethyl 1,1-cyclopropanedicarboxylate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1559-02-0

Example 91 2″-amino-6′-(5-chloropyrid-3-yl)-l”-methyldispiro[cyclopropane-l,3′-chroman-4′,4″- imidazol]-5′(l’H)-oneStep A: A mixture of diethyl cyclopropane-l,l-dicarboxylate (14.1 mL, 80.6 mmol) and lithium tri-tert- butoxyaluminohydride (201.4 mL, 201.4 mmol) was heated to reflux in THF for 3 hours. The mixture was cooled down and partitioned between water and EtOAc. The organics were washed with water, brine and dried with Na2S04. This was concentrated down and then purified on a column using 10 to 50% EtOAc:hexanes to give ethyl l-(hydroxymethyl)cyclopropanecarboxylate (1.5 g, 10.4 mmol, 12.9%) as an 12.9%) as an oil.

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, 1559-02-0, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; HUNT, Kevin, W.; RIZZI, James, P.; COOK, Adam; WO2011/72064; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 15963-46-9, 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. 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-(1-(pentan-3-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrazine (0.100 g, 0.311 mmol) and methyl 3-chlorocyclobutanecarboxylate (0.0925 g, 0.622 mmol) in DMF (1.56 mE, 0.311 mmol) was added cesium carbonate (0.203 g, 0.622 mmol) and the reaction mixture was stirred at 80 C for 5 hours. The reaction mixture was cooled to ambient temperature, diluted with water (15 mE) and stirred for 10 minutes. The reaction mixture was extracted with EtOAc and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (50% EtOAc/hexanes) to afford two isomers. Faster eluting peak: trans-methyl 3-(4-(4-(1-(pentan- 3 -yl)- 1 H-pyrazol-4-yl)pyrazolo [1 ,5-ajpyrazin-6-yl)- I H-pyrazol- 1 -yl)cyclobutanecarboxylate(28 mg, 21% yield) as an off-white foam. Slower eluting peak: cis-methyl 3-(4-(4-(1-(pentan- 3-yl)-l H-pyrazol-4-yl)pyrazolo [1 ,5-a]pyrazin-6-yl)- 1 H-pyrazol- 1 -yl)cyclobutanecarboxylate(58mg, 43% yield) as a thick oil.

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-chlorocyclobutanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 2495-35-4,Some common heterocyclic compound, 2495-35-4, name is Benzyl acrylate, molecular formula is C10H10O2, 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: The catalyst precursor in form of a 0.04 M CuSO4 and 0.004 M CoCl2 solution was added to a solution of the alkene/alkyne compound in methanol. The reaction was started by adding an initial portion of NaBH4, resulting in a color change to black (in situ prepared catalyst) and vigorous gas evolution. Additional portions of NaBH4 were added in intervals of typically three or four minutes. The reaction itself was carried out at room temperature and normal atmosphere. However, generation of heat due to the exothermic character of the reaction usually heated the reaction mixture to 30-40 C. Cooling is generally not necessary in small scale. For large scale reactions a reflux condenser was used. The higher reaction temperature did not influence the reaction yield. The reaction mixture was finally quenched by adding 2 M H2SO4. Work up was carried out by extracting the water/methanol phase with DCM. The catalyst in general stays within the water/methanol layer. Drying the DCM layer with MgSO4 followed by filtration removes all remaining catalyst particles. The drying agent was filtered of and the DCM was removed in vacuo.

The synthetic route of 2495-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ficker, Mario; Svenningsen, S°ren W.; Larribeau, Thomas; Christensen, J°rn B.; Tetrahedron Letters; vol. 59; 12; (2018); p. 1125 – 1129;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 454-31-9,Some common heterocyclic compound, 454-31-9, name is Ethyl 2,2-difluoroacetate, molecular formula is C4H6F2O2, 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.

Step 2 Preparation of 4,4-difluoro-1-(3-fluoro-4-methoxyphenyl)-butane-1,3-dione Ethyl difluoroacetate (4.06 g, 32.7 mmol) was dissolved in methyl tert-butyl ether (50 mL). To the stirred solution was added 25 weight % sodium methoxide (7.07 g, 32.7 mmol) followed by 3′-fluoro-4′-methoxyacetophenone from Step 1 (5.0 g, 29.7 mmol). After stirring for 16 hours, 1N HCl (50 mL) was added. The organic layer was collected and washed with water (2*50 mL), dried over anhydrous MgSO4, filtered, and added to hexanes to precipitate a tan solid (7.0 g, 96%): mp 70-72 C.

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

Reference:
Patent; G. D. Searle & Co.; US6376528; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, molecular formula is C8H6BrFO2, 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. COA of Formula: C8H6BrFO2

To methyl 3-bromo-4-fluorobenzoate (3.02 g, 13.0 mmol) in ether (30 ml) at 0 C. add dropwise MeMgBr (3.0M in ether, 11 ml, 33 mmol). Stir 1 h and pour onto ice. Acidify with 1N HCl, separate the ether, wash with 1N NaHCO3, dry (MgSO4), and concentrate to obtain the product as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 82702-31-6, its application will become more common.

Reference:
Patent; Schering Corporation; US2005/239795; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics