Month: June 2021

Related Products of 150529-73-0, The chemical industry reduces the impact on the environment during synthesis 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, I believe this compound will play a more active role in future production and life.

Step 2: [00153] To a solution of the ester (6.0 g, 26.2 mmol) in tert-butanol (24 ml_) was added, under nitrogen atmosphere, sodium iodide (7.8 g, 52.4 mmol), N1N’- dimethylethylenediamine (0.3 ml_, 2.6 mmol) and copper iodide (0.3 g, 1.3 mmol). The reaction mixture was heated in a microwave apparatus at 145C for 1 h. Water (100 mL) was added and the product was extracted with ethyl acetate (3 x 50 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was purified by flash chromatography on silica gel with a mixture of hexanes/ethyl acetate (8:2). This gave 3- iodophenylacetic acid methyl ester as a colorless oil (6.6 g, 86%). 1H NMR (400 MHz, CDCI3): d = 7.63 (m, 1 H), 7.58-7.61 (m, 1 H)1 7.23-7.26 (m, 1 H)1 7.05 (dd, J = 7.8 Hz, 1 H), 3.69 (s, 3H), 3.56 (s, 2H); LRMS (ESI): m/z = 277 (MH+).

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

Reference:
Patent; PROMETIC BIOSCIENCES INC.; ZACHARIE, Boulos; PENNEY, Christopher; GAGNON, Lyne; BIENVENU, Jean-Francois; PERRON, Valerie; GROUIX, Brigitte; WO2010/127440; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 139102-34-4 as follows. name: Methyl 4-bromo-2-methoxybenzoate

A solution of 4-bromo-2-methoxybenzoic acid methyl ester (0.1 mol) and tetrahydro- 2H”-pyran-4-amine (0.3 mol) in 1 -methyl-2-pyrrolidinone (800 ml) was stirred at 400C. Cs2CO3 (0.2 mol) was added. The reaction mixture was stirred for 5 minutes. Pd2(dba)3 (0.002 mol) and BINAP (0.003 mol) were added. The reaction solution was degassed by applying alternating nitrogen atmosphere and vacuum. The reaction mixture was stirred overnight at 110C. The 1 -methyl-2-pyrrolidinone solvent was evaporated. The residue was purified by high-performance liquid chromatography. The product fractions were collected and the solvent was evaporated, yielding 13 g of intermediate (29).

According to the analysis of related databases, 139102-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/62990; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route 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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 110-38-3,Some common heterocyclic compound, 110-38-3, name is Ethyl caprate, molecular formula is C12H24O2, 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 16 (PREPARATION OF DECANOL) A dry Schlenk tube under argon was charged with 51 mg (0.15 mmol) of dysprosium (III) isopropoxide. Triethoxysilane (1.4 mL, 7.5 mmol) and ethyl decanoate (696 muL, 3 mmol) were added and the reaction mixture was heated to 60 C. After 29 hours, GLC analysis of an aliquot taken from the reaction mixture showed 23% conversion. The reaction mixture was then heated to 70 C. After an additional 3 days, THF (8 mL) and aqueous NaOH (1 N, 15 mL) were added, and the mixture was stirred vigorously for 3 hours. The reaction was worked up as in Example 13. Purification by flash chromatography (ether:hexane=3:7) afforded 224 mg (47% yield) of decanol (>95% pure by 1 H-NMR analysis) and 40 mg of recovered starting material (84% pure, 5.5% yield).

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

Reference:
Patent; Massachusetts Institute of Technology; US5220020; (1993); A;,
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., category: esters-buliding-blocks

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;,
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. 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H8BrNO2

To a 250 mL round-bottom flask was added methyl 4-amino-3-bromobenzoate 32a (2.4 g, 10.43 mmol, 1.00 equiv.), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-l,3,2- dioxaborolane (2.6 g, 12.38 mmol, 1.20 equiv.), dioxane (100 mL), aq. sodium bicarbonate (37 mL, 3.50 equiv, 1M), and Pd(PPh3)4 (1.21 g, 1.05 mmol, 0.10 equiv.). The resulting mixture was heated at 100C overnight. After cooling to room temperature, the mixture was diluted with 300 mL of EA and washed with brine (200 mL x 2). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by Flash-Prep- HPLC using the following conditions (IntelFlash-1): Column, silica gel; mobile phase, PE_EA=100:0 increasing to PE_EA=50:50 within 30 min; Detector, UV 254 nm. Removal of solvents afforded methyl 4-amino-3-(3,6-dihydro-2H-pyran-4-yl)benzoate 32b (2.4 g, 99% as a white solid.

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; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products 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

Adding a certain compound to certain chemical reactions, such as: 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, 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 18595-12-5, Recommanded Product: 18595-12-5

Combine methyl 2-methyl-5-aminobenzoate (4.5 g, 27.2 mmol) and triethyl orthoformate (16.2 g, 109 mmol) in glacial acetic acid (25 mL). After 12 hours, add portionwise sodium azide (7.08 g, 109 mmol). Heat to 70 C. After 2 hours, cool the reaction mixture to ambient temperature, dilute with water (250 mL). Collect the solid by filtration, rinse with water, and dry to give methyl 2-methyl-5-(1H-tetrazol-1-yl)benzoate: Rf=0.13 (silica gel, ethyl acetate/hexane 1/4).

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; Maynard, George D.; Le, Tieu-Binh; US2001/34343; (2001); A1;; ; Patent; Aventis Pharmaceuticals Inc.; US6194406; (2001); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference 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

Some common heterocyclic compound, 87639-57-4, name is Dimethyl 4-bromophthalate, molecular formula is C10H9BrO4, 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: C10H9BrO4

Example 1; Compound No. 1: Synthesis of 4-phenyl ethynyl dimethyl phthalate; Under a nitrogen gas stream, 24.6 g of 4-bromo-dimethyl phthalate, 11.03 g of ethynyl benzene, 71 mg of triphenylphosphine, 20 mg of trans-dichloro-bis (triphenylphosphine)palladium (II) and 171 mg of cuprous iodide were placed in a three-necked flask of 300-ml capacity and, then, 60 ml of triethylamine was poured therein while stirring. The reaction mixture was refluxed for 12 hours while heating at 100 C., cooled to room temperature and, thereafter, the resultant reaction solution was filtered to remove formed salts and catalysts and, then, washed with 60 ml of toluene. The filtrate and a rinsing solution were combined and concentrated, to obtain 25.1 g of a crude crystal of 4-phenyl ethynyl diethyl phthalate. The thus-obtained crude crystal was recrystallized from a mixed system comprising 2-propanol/n-hexane (50 ml/100 ml), to thereby obtain 22.9 g of 4-phenyl ethynyl diethyl phthalate. The yield thereof was 86.4%. 1H-NMR (CDCl3): 3.92 ppm (s, 3H), 3.93 ppm (s, 3H), 7.36 to 7.39 ppm (m, 3H), 7.52 to 7.56 ppm (m, 2H), 7.66 ppm (q, 1H), 7.75 ppm (d, 1H), 7.85 ppm (d, 1H) IR vmax (KBr): 1269 (s), 1604 (m), 1724 (s), 2210 (w), 2950 (w), 3003 (w) cm-1 MS: m+/z=295 Melting point: 76.9 C. to 77.4 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 87639-57-4, its application will become more common.

Reference:
Patent; FUJI PHOTO FILM CO., LTD.; US2005/215820; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics