Month: June 2021

Synthetic Route of 10602-03-6, A common heterocyclic compound, 10602-03-6, name is Ethyl 4-ethynylbenzoate, molecular formula is C11H10O2, 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.

Step 3-Preparation of 4-[1-Benzenesulfonyl-5-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-3-ylethynyl]-benzoic acid ethyl ester 135 1-Benzenesulfonyl-5-(3,4-dimethoxy-phenyl)-3-iodo-1H-pyrrolo[2,3-b]pyridine (0.0800 g, 0.000151 mol), 4-Ethynyl-benzoic acid ethyl ester (0.0321 g, 0.000181 mol), Bis(triphenylphosphine)palladium(II) chloride (0.0048 g, 0.0000069 mol), and Copper(I) iodide (0.00024 g, 0.0000013 mol) were dissolved in Triethylamine (0.8 mL, 0.005 mol) under an atmosphere of Nitrogen. The resulting mixture was heated to 60 C. and stirred under an atmosphere of Nitrogen for 2 hours. The reaction mixture was was concentrated under reduced pressure and water (30 mL) was added to the residue. This slurry was extracted with ether. (20 mL 2*). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude was purified by chromatography (Silica gel, ethyl acetate/hexanes to give 85 mg of the titled product as a pale orange solid. MS(ESI) [M+H+]+=567.10

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; Ibrahim, Prabha N.; Bremer, Ryan; Gillette, Sam; Cho, Hanna; Nespi, Marika; Mamo, Shumeye; Zhang, Chao; Artis, Dean R.; Lee, Byunghun; Zuckerman, Rebecca; US2006/100218; (2006); 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. 52449-43-1, name is Methyl 4-chlorophenylacetate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

a) At 35 C. a solution of 4-chlorophenylacetic acid methyl ester (52 g) in THF (170 ml) was carefully added over a period of 70 min to a suspension of NaH (15.6 g) in dry THF (550 ml). Stirring was continued for 40 min without heating and the temperature dropped to 290C. The evolution of gas had stopped before dimethylcarbonate (94.8 ml) was added dropwise while the temperature of the mixture was maintained at 25-28 C. After the evolution of gas had ceased, the mixture was diluted with THF (200 ml) and stirring was continued for 72 h at rt. The mixture was carefully acidified with aq. HCl before bulk of the THF was removed in vacuo. The residue was dissolved in diethyl ether (1200 ml), washed three times with 1 N aq. HCl and once with brine, dried over MgSO4 and evaporated. The residue formed was collected, washed with diethyl ether and dried to give 2-(4-chloro-phenyl)-malonic acid dimethyl ester (42 g) as white crystals.

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; Weller, Thomas; Bolli, Martin; Boss, Christoph; Clozel, Martine; Fischli, Walter; US2004/102464; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 27007-53-0, name is Methyl 2-bromo-5-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 2-bromo-5-chlorobenzoate

To a stirred solution of methyl 2-bromo-5-chlorobenzoate (10 g, 40.1 mmol) in 1,4-dioxane (50 mL) cooled to -10 C. was added bis(pinacolato)diboron (12.21 g, 48.1 mmol) and PdCl2(dppf) (1.466 g, 2.004 mmol) followed by potassium acetate (11.80 g, 120 mmol). The mixture was then heated to 90 C. overnight. The reaction mixture was cooled to room temperature, diluted with water (300 mL) and extracted with ethyl acetate (500 mL). The organic layer was separated and dried over sodium sulphate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10% ethyl acetate in petroleum ether) to afford methyl 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (11.8 g, 39.8 mmol, 99% yield). LC/MS (ESI) m/e 297.2 [(M+H)+, calcd for C14H19BClO4, 297.1]; LC/MS retention time (Method A1): tR=2.32 min; 1H NMR (400 MHz, CHLOROFORM-d) delta 7.92 (d, J=2.0 Hz, 1H), 7.49 (dd, J=8.0, 2.0 Hz, 1H), 7.45-7.41 (m, 1H), 3.92 (s, 3H), 1.41 (s, 12H).

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 27007-53-0.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Nara, Susheel Jethanand; Dzierba, Carolyn Diane; Macor, John E.; Bronson, Joanne J.; Ramkumar, Rajamani; Maishal, Tarun Kumar; Karatholuvhu, Maheswaran Sivasamban; Thangavel, Soodamani; Thiyagarajan, Kamalraj; (77 pag.)US2018/141956; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6065-82-3, name is Ethyl diethoxyacetate, 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 6065-82-3, Product Details of 6065-82-3

Nine reactions were carried out in parallel and combined for work-up. A solution of 32 1-bromo-3,5-difluorobenzene (100 g, 518 mmol) in 15 THF (700 mL) was degassed and purged with 33 nitrogen three times. Then 2 M 34 LDA (311 mL) was added at -70 C. and the reaction mixture was stirred at -70 C. for 0.5 h under nitrogen. A solution of 35 ethyl 2,2-diethoxyacetate (96 g, 544 mmol) in THF (200 mL) was added drop-wise at -70 C. under nitrogen and the reaction mixture was stirred for 1 h. The reactions were combined and poured into ice saturated 36 ammonium chloride (10 L) in portions and extracted with EtOAc (3×3 L). The organic layer was separated, washed with brine (5 L), dried over sodium sulfate, concentrated, and purified by silica gel chromatography (eluted with petroleum ether EtOAc 1:0-100:1) to give the 37 title compound (1.26 kg, 84% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.12 (d, J=7.2 Hz, 2H), 5.15 (s, 1H), 3.61-3.7 (m, 4H), 1.2 (t, J=7.2 Hz, 6H).

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; THERAVANCE BIOPHARMA R&D IP, LLC; FATHEREE, PAUL R.; JIANG, LAN; MCKINNELL, ROBERT MURRAY; THALLADI, VENKAT R.; ZHANG, HAO; DABROS, MARTA; NZEREM, JERRY; BENJAMIN, NOAH; KLEINSCHEK, MELANIE A.; CRATER, GLENN D.; (40 pag.)US2018/311255; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 61644-18-6, 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. 61644-18-6 name is Chloromethyl isobutyrate, 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.

General procedure: Carboxylic acid (±)-9 (5.18 mmol) was dissolved in N,N-dimethylformamide (15.5 mL). Cesium carbonate (4.14 mmol) was added to the solution and the suspension was stirred during 2-3 min after which chloromethyl 2-methylpropanoate (6.73 mmol) was added. After stirring at room temperature during 18-24 h, dichloromethane (30 mL) was added to the mixture and the resulting organic phase was successively washed with water (3×20 mL) and brine (3×20 mL). Organic solvent was eliminated and the residue was submitted to flash chromatography (hexane/ethyl acetate mixtures) to yield the corresponding diester (±)-5.

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

Reference:
Article; Torres, Susana Y.; Ochoa, Estael; Verdecia, Yamila; Rebolledo, Francisca; Tetrahedron; vol. 70; 31; (2014); p. 4675 – 4684;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 122-72-5, name is 3-Phenylpropyl Acetate, 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 122-72-5, Safety of 3-Phenylpropyl Acetate

(b) 3-(p-Iodophenyl)Propanol Using the procedure outlined in Example 1, 3-phenyl propyl acetate was converted to 3-(p-iodophenyl)propanol (ND25 =1.6048).

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, 3-Phenylpropyl Acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lafayette Pharmacal Inc.; US4175544; (1979); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 35450-36-3, 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. 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of Cs2CO3 (2 mmol) in H2O (5 mL) were added methyl 2-bromobenzoate (1a, 1 mmol), 1H-pyrazol-5-amine (2a, 1.2 mmol), and CuI (0.2 mmol). The mixture was stirred at 100 C under nitrogen atomasphere until a complete conversion as indicated by TLC. It was cooled to room temperature and then extracted with ethyl acetate. The combined organic phase was dried over anhydrous Na2SO4, and concentrated under vacuum. The crude product was purified by column chromatography eluting with petroleum ether/ethyl acetate (3:1) to give 3a. Products 3b-3t and 6 were obtained in a similar manner.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-5-methoxybenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Xinying; Gao, Lin; Wang, Zhangxin; Fan, Xuesen; Synthetic Communications; vol. 45; 21; (2015); p. 2426 – 2435;,
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Ester – an overview | ScienceDirect Topics

Synthetic Route of 2672-58-4,Some common heterocyclic compound, 2672-58-4, name is Trimethyl benzene-1,3,5-tricarboxylate, molecular formula is C12H12O6, 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 Trimethyl 1,3,5-Benzenetricarboxylate (1.1 g, 4.36 mmol) in MeOH (100 mL) wasadded 1 M NaOH aq. (3.95 mL, 3.95 mmol). The solution was stirred for 22 h at rt. After removal ofthe solvent by evaporation, the mixture was washed with CH2Cl2. The aqueous layer was acidified with 6 M HCl to pH 2 and then extracted with AcOEt. The organic layer was dried over Na2SO4 andthe solution was concentrated by evaporation to give 17 (849 mg, 79%) as a white solid.

The synthetic route of 2672-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zenmyo, Naoki; Tokumaru, Hiroki; Uchinomiya, Shohei; Fuchida, Hirokazu; Tabata, Shigekazu; Hamachi, Itaru; Shigemoto, Ryuichi; Ojida, Akio; Bulletin of the Chemical Society of Japan; vol. 92; 5; (2019); p. 995 – 1000;,
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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 7459-46-3 as follows. category: esters-buliding-blocks

To a solution of compound 30 (495 g, 2.01 mol) in tert-butanol (4 L) was added NaBH4 (434 g, 12.04 mol) with vigorous stirring at RT under N2 atmosphere. To this stirred solution was added methanol (250 mL) in three portions during 45 mins maintaining a gentle reflux. The reaction mixture was slowly warmed to 80 °C and allowed to reflux at the same temperature for over night. The reaction mixture was cooled, added 5M hydrochloric acid to get pH = 7 (app). The mixture was filtered, the residue washed with ethanol (2 x 500 mL) and combined the organic layers. The solvent was removed under vacuum and the crude product was purified by column chromatography on silica gel (10percent methanol in chloroform) to give the title compound (160 g, 66percent). TLC: Chloroform/Methanol, 4: 1, Rf=0.2

According to the analysis of related databases, 7459-46-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEDIVIR AB; WO2005/65689; (2005); 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. 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C11H14ClNO2

To a solution of (3R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1 .0]hexane-3- carboxylic acid (syn-anti diastereoisomer mixture 10/2) (D27) (3.06 g, 13.5 mmol) in dry DMF (15 ml) under N2 atmosphere HOBT.H20 (2.06 g, 13.46 mmol), EDC.HCI (3.87 g, 20.20 mmol), methyl 4-(1 -aminocyclopropyl)benzoate hydrochloride (3.06 g, 13.46 mmol) and TEA (4.7 ml, 33.7 mmol) were added in sequence. The mixture was stirred for 2 hrs at RT, then the solvent was evaporated in vacuo and the residue taken up in AcOEt (500ml), washed twice with water (50 ml), dried over Na2SO4 and evaporated to afford a residue which was loaded on a SNAP-Si cartridge (100g) and eluted with a mixture DCM/AcOEt from 10/0 to 9/1 . Collected fractions after solvent evaporation afforded the two diastereoisomer (D73a) (2.55 g) and (D73b) (880 mg). (D73a) (syn diastereoisomer) MS: (ES/+) m/z: 401 .4 [MH+] C22H28N2O5 requires 400.20 1 H NMR (400 MHz, DMSO-d6) delta (ppm): 8.70 (s, 1 H), 7.90 – 7.76 (m, 2 H), 7.34 – 7.19 (m, 2 H), 4.52 – 4.35 (m, 1 H), 3.84 (s, 3 H), 3.43 – 3.32 (m, 1 H), 2.67 -2.39 (m, 1 H), 1 .88 – 1 .74 (m, 1 H), 1 .52 – 1 .33 (m, 10 H), 1 .27 – 1 .12 (m, 4 H), 1 .09 – 0.92 (m, 1 H), 0.66 – 0.53 (m, 1 H). (D73b) (anti diastereoisomer) MS: (ES/+) m/z: 401 .4 [MH+] C22H28N2O5 requires 400.20 1 H NMR (400 MHz, DMSO-d6) delta (ppm): 8.69 – 8.52 (s, 1 H), 7.90 – 7.73 (m, 2 H), 7.35 – 7.19 (m, 2 H), 3.93 – 3.75 (m, 4 H), 3.36 – 3.30 (m, 1 H), 2.35 – 2.19 (m, 1 H), 2.12 – 2.02 (m, 1 H), 1 .90 – 1 .74 (m, 1 H), 1 .47 – 1 .30 (m, 9 H), 1 .25 – 1 .07 (m, 4 H), 0.73 (td, J = 5.4, 8.8 Hz, 1 H), 0.39 (br. s., 1 H).

The synthetic route of 1014645-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; PUCCI, Sabrina; STASI, Luigi, Piero; ROVATI, Lucio; WO2013/4290; (2013); A1;,
Ester – Wikipedia,
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