Tag: M.W=200-300

Some common heterocyclic compound, 653-92-9, name is Methyl 2-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. 653-92-9

To a solution of methyl 2-bromo-4-fluoro-benzoate (90 g, 386.21 mmol, 1 eq) in dimethylsulfoxide (500 mL) was added tert-butyl piperazine-1-carboxylate (111.82 g, 502.07 mmol, 1.3 eq, hydrochloric salt) and N,N-diisopropylethylamine (199.66 g, 1.54 mol, 269 mL, 4 eq). The mixture was heated to 130 C and stirred at 130 C for 36 hours. The mixture was poured into 1.0 L water, and extracted with ethyl acetate (500 mL x 2). The organic layer was washed with water (1000 mL), 0.5 M hydrochloric acid (500 mL), saturated brine (500 mL) and then dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was triturated with (petroleum ether : ethyl acetate =5:1, 300 mL), the solid was filtered and dried in vacuum. tert-butyl 4-(3-bromo-4-methoxycarbonyl-phenyl)piperazine-1-carboxylate (93 g, 232.92 mmol, 60% yield) was obtained as an off-white solid. LC/MS (ESI) m/z: 422.1 [M+23] +; 1H-NMR (400MHz, DMSO-d6) d 7.73 (d, J=8.8 Hz, 1H), 7.18 (d, J=2.4 Hz, 1H), 6.98 (dd, J=8.8, 2.4 Hz, 1H), 3.77 (s, 3H), 3.45-3.42 (m, 4H), 3.34-3.31 (m, 4H), 1.42 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 653-92-9, its application will become more common.

Reference:
Patent; ARVINAS OPERATIONS, INC.; YALE UNIVERSITY; CREW, Andrew P.; HORNBERGER, Keith R.; WANG, Jing; CREWS, Craig M.; JAIME-FIGUEROA, Saul; DONG, Hanqing; QIAN, Yimin; ZIMMERMAN, Kurt; (1451 pag.)WO2020/51564; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

24398-88-7, name is Ethyl 3-bromobenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 24398-88-7

Step 1 : Ethyl 3-(3-methoxypropyl)benzoateTo a THF solution (0.1 M) of allyl methyl ether (1.4 eq.) was added, at 0 0C, 9- borabicyclo[3.3.1]nonane (2.4 eq.) over a period of 30 min. The solution was stirred at 0 0C for 1 h and then warmed slowly to RT over 16 h. To the resulting clear solution was then added sodium methoxide (2.4 eq.), Cl2Pd(dppf)-dichloromethane complex (5% loading) and ethyl 3-bromobenzoate (1 eq.). The now brown suspension was heated to reflux for 16 h. The reaction mixture was cooled to RT, quenched with sat. aq. NH4Cl and extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a brown oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex -^ 4: 1 (v/v) Hex : EtOAc) afforded the title compound as a light yellow oil.

Statistics shows that 24398-88-7 is playing an increasingly important role. we look forward to future research findings about Ethyl 3-bromobenzoate.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2007/9250; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

51329-15-8, name is Methyl 3,5-dibromobenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 51329-15-8

A mixture of compound 2 (5.6 g, 19.2 mmol), PMBSH (3.8 g, 24.7 mmol), Pd2(dba)3 (1.7 g, 1.9 mmol), Xantphos (2.2 g, 3.8 mmol) and DIPEA (4.9 g, 38.0 mmol) in 1,4-dioxane (100 mL) was heated to 100 C. for 16 h. The reaction mixture was concentrated under vacuum, and purified by column chromatography to give the compound 3 (3.9 g, 56%).

Statistics shows that 51329-15-8 is playing an increasingly important role. we look forward to future research findings about Methyl 3,5-dibromobenzoate.

Reference:
Patent; Novira Therapeutics, Inc.; Hartman, George D.; US2015/225355; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

541-16-2, 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 541-16-2 as follows.

2) Preparation of 2-cyclopropylmethyl-4-[2,2-di(tert-butoxycarbonyl)ethyl]-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one After 55% sodium hydride (322 mg, 7.38 mmol) was added to a solution of di-tert-butyl malonate (970 mg, 4.48 mmol) in N,N-dimethylformamide (10 mL), 4-bromomethyl-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphen yl)-2H-pyridazin-3-one (1.8 g, 4.90 mmol) was added under ice-cold stirring. The reaction mixture was stirred at room temperature for 1 hour, poured into water, and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was isolated and purified by chromatography on silica gel (hexane/ethyl acetate=3/1) to yield the title compound as a yellow powder (yield: 1.39 mg, 61.8%). 1H NMR (400 MHz, CDCl3) delta: 0.44-0.50 (2H, m), 0.50-0.58 (2H, m), 1.41 (18H, s), 1.56 (1H, m), 3.12 (2H, d, J=7.8 Hz), 3.87 (1H, t, J=7.8 Hz), 3.94 (3H, s), 4.09 (2H, d, J=7.8 Hz), 7.01 (1H, dd, J=8.5, 8.5 Hz), 7.43 (1H, d, J=8.5 Hz), 7.50 (1H, s), 7.57 (1H, dd, J=12.4, 2.2 Hz).

According to the analysis of related databases, Di-tert-Butyl malonate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KOWA CO., LTD.; US2004/2497; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

15964-79-1, Adding a certain compound to certain chemical reactions, such as: 15964-79-1, name is Methyl 2-(3,4-dimethoxyphenyl)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 15964-79-1.

General procedure: To a mixture corresponding ester (9a-n, 5.0 mmol) and hydrazine monohydrate (15.0 mmol) in ethanol, catalytic amount of pyridine (0.5 mL) was added and refluxed for 10 h. The reaction was monitored by TLC. After the completion of the reaction, ethanol was evaporated from the mixture, water was added and extracted using ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under vacuum to get the crude mass. Finally, the products 10a-n were purified using column chromatography. (Yield 80-85%).

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-(3,4-dimethoxyphenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Manickam, Manoj; Boggu, Pulla Reddy; Pillaiyar, Thanigaimalai; Sharma, Niti; Jalani, Hitesh B.; Venkateswararao, Eeda; Jung, Sang-Hun; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2369 – 2374;,
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. 2905-54-6, name is Methyl 2,3-dichlorobenzoate, A new synthetic method of this compound is introduced below., 2905-54-6

A suspension of 10.56 g of lithium aluminium hydride in 125 ml of THF is cooled to 0 C., a solution of 25.68 g of the compound obtained in the preceding step in 100 ml of THF is added dropwise, the temperature is allowed to return to RT and the mixture is kept stirred for 2 hours at RT. The reaction mixture is diluted by adding 250 ml of THF and hydrolysed by adding 11 ml of water, 11 ml of 4N NaOH and 33 ml of water. It is allowed to stand overnight at RT, the inorganic salts are filtered and the filtrate is concentrated under vacuum. 21.54 g of the expected product are obtained after drying under vacuum at 30 C.

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; Emonds-Alt, Xavier; Proietto, Vincenzo; US2004/180890; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, I believe this compound will play a more active role in future production and life. 14062-25-0

Step a: Diethyl 2-(4-bromophenyl)malonate To a solution of ethyl 2-(4-bromophenyl)acetate (5.0 g, 21 mmol) in dry THF (40 mL) at -78 C. was added a 2.0M solution of lithium diisopropylamide in THF (11 mL, 22 mmol). After stirring for 30 minutes at -78 C., ethyl cyanoformate (2.0 mL, 21 mmol) was added and the mixture was allowed to warm to room temperature. After stirring for 48 h at room temperature, the mixture was quenched with water (10 mL). The reaction was partitioned between 1 N HCl (50 mL) and dichloromethane (50 mL), and the organic layer was separated. The organic layer was washed with 1 N HCl (50 mL), dried over Na2SO4 and evaporated. The crude material was purified by silica gel chromatography, eluding with 0-20% ethyl acetate in hexanes to give diethyl 2-(4-bromophenyl)malonate (2.6 g, 41%) 1H NMR (400 MHz, DMSO-d6) delta 7.60-7.58 (m, 2H), 7.36-7.34 (m, 2H), 5.03 (s, 1H), 4.21-4.09 (m, 4H), 1.20-1.16 (m, 6H).

The chemical industry reduces the impact on the environment during synthesis 14062-25-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hadida Ruah, Sara S.; Miller, Mark T.; Bear, Brian; McCartney, Jason; Grootenhuis, Peter D. J.; US2008/9524; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 2876-78-0, name is Methyl 1-Naphthaleneacetate, 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 2876-78-0. 2876-78-0

alpha-(N-tert-Butoxycarbonyl-6-amino-1-hexyl)-alpha-(1-naphthyl)-acetic acid methyl ester alpha-(1-Naphthyl)-acetic acid methyl ester (150 mg, 0.75 mmol) was dissolved in tetrahydrofuran. To the solution, hexamethylphosphoramide (HMPA, 671 mg, 3.75 mmol) was added, and the mixture was cooled to -78 C. To this solution, lithium diisopropylamide (1.5 M solution in cyclohexane, 0.75 ml, 1 mmol) was added dropwise, and the mixture was stirred at -78 C. for 30 minutes. Then, a tetrahydrofuran solution (2 mL) of N-tert-butoxycarbonyl-6-amino-1-iodohexane (270 mg, 0.82 mmol) was added dropwise thereto, and the mixture was stirred at -78 C. for 1 hour. The temperature of the reaction solution was raised to 0 C. over 15 minutes, and then, water (50 mL) was added to the solution, followed by extraction with ethyl acetate (50 mL) twice. The organic layer was washed with a saturated ammonium chloride solution (20 mL) and subsequently brine (20 mL) and then dried over sodium sulfate to dryness under reduced pressure. The reaction product was purified by silica gel column chromatography (hexane:ethyl acetate=8:2) to obtain alpha-(N-tert-butoxycarbonyl-6-amino-1-hexyl)-alpha-(1-naphthyl)-acetic acid methyl ester (271 mg, yield: 91%): 1H NMR (400 MHz, CDCl3): delta 8.11 (d, J=8.5 Hz, 1H), 7.83 (d, J=8.0 Hz, 1H), 7.74 (d, J=8.1 Hz, 1H), 7.40-7.54 (m, 4H), 4.71 (s, 1H), 4.36 (t, J=7.8 Hz, 1H), 3.61 (s, 3H), 3.04 (m, 2H), 2.07 (m, 2H), 1.24-1.48 (m, 17H); 13C NMR (100 MHz, CDCl3): delta 174.7, 155.9, 135.3, 133.8, 131.3, 128.8, 127.5, 126.1, 125.4, 125.3, 124.6, 122.8, 78.7, 51.8, 46.5, 40.3, 32.9, 29.7, 28.9, 28.2, 27.6, 26.3; FAB-MS: m/z [M+H]+ 400.

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 Methyl 1-Naphthaleneacetate.

Reference:
Patent; TOHOKU UNIVERSITY; KAKE EDUCATIONAL INSTITUTION; KANAGAWA PREFECTURAL HOSPITAL ORGANIZATION KANAGAWA CHILRDEN’S MEDICAL CENTER; ABE, Takaaki; TOMINAGA, Teiji; HAYASHI, Kenichiro; OSAKA, Hitoshi; US2015/353489; (2015); 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. 1459-96-7, name is Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, This compound has unique chemical properties. The synthetic route is as follows., 1459-96-7

To the stirred solution of dimethyl bicycle [2.2.2] octane-1, 4-dicarboxylate (6.35 g, 28.1 mmol) in MeOH (60 mL) and Water (12 mL) was added barium hydroxide octahydrate (4.43 g, 14.03 mmol) and the reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with water (150 mL) and extracted with hexane (2 x 100 mL). The aqueous layer was acidified with 1.5 N HC1 and extracted with EtOAc (2 x 200 mL). The organic layer was dried over Na2S04and concentrated under reduced pressure. The residue was stirred with toluene (100 mL) and filtered. The filtrate was concentrated under reduced pressure to yield 4-(methoxycarbonyl) bicycle [2.2.2] octane- 1 -carboxylic acid (3.5 g, 16.49 mmol, 58.8 % yield) as white solid.

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; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

24398-88-7, Adding some certain compound to certain chemical reactions, such as: 24398-88-7, name is Ethyl 3-bromobenzoate, 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 24398-88-7.

3-bromobenzoicacid ethyl ester 25 (1.5g, 6.6mmol) was dissolved in 15mL of ethanol, then under ice-cooling was slowly added dropwise with hydrazine hydrate (1.3g,26mmol), after the addition was complete, it was stirred at room temperaturefor 15min, then heated under reflux for 10h. After completion of the reaction, ethanol was removed by rotary evaporation, poured into water, extracted with ethyl acetate, the organic phase was dried and concentrated to give the desired product 26 (1.1g, 78%), without purification into the next step.

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 24398-88-7.

Reference:
Patent; Jiangshu Alpha Biopharmaceuticals, Inc.; Jiangnan University; Nanjing Drum Tower Hospital; Feng, Bainian; Yang, Guijun; Tang, Chunlei; Wang, Guping; Jie, Desheng; (36 pag.)CN105481765; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics