Month: March 2021

Some common heterocyclic compound, 5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate, molecular formula is C7H12O3, 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. Safety of Ethyl (E)-3-Ethoxyacrylate

To a reactor was charged K3PO4 (4104 g granular, 19.3 moles), ethyl 3-amino-lH-pyrazole-4-carboxylate (2000 g, 12.9 moles), and DMF (18.8 kg) and the mixture was agitated. After 20 min, (?)- ethyl 3-ethoxyacrylate, (2230 g, 15.5 moles) was added and the mixture was heated to 110- 115 C internal temperature (IT). After the reaction was judged to be complete based on consumption of starting material, heating was ceased. The mixture was allowed to stir and cool overnight. Aqueous hydrochloric acid (3 M, 13 L) was added over ~ 2 h. DI water (6 L) was added and the mixture was allowed to stir overnight. The mixture was filtered through polypropylene filter cloth (PPFC) and the residue was washed with water (3 x 5 vol, 3 x 10 L). The solid was placed in trays and oven dried under vacuum at 55 C for 3 days and then 45 C for 4 days to constant wei ht of (2553 g 95.6%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5941-55-9, its application will become more common.

Reference:
Patent; ZHAO, Qian; SPENCER, Stacey; JIANG, Yutong; HAAS, Julia; EARY, Charles Todd; (352 pag.)WO2019/84285; (2019); A1;,
Ester – Wikipedia,
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Application of 40872-87-5, 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. 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 3 Synthesis of 3-cyclopentyl-1-methyl-2-pyridin-2-yl-1H-indole-6-carboxylic acid methyl ester (13) A 100 mL three neck flask equipped with a thermocouple, condenser and stir bar was purged with argon. 3-Amino-4-chlorobenzoic acid methyl ester (5.0 g, 26.94 mmol), 2-cyclopentylethynyl-pyridine (5.528 g, 32.33 mmol), Pd(OAc)2 (181 mg, 0.81 mmol), DtBPF (767 mg, 1.62 mmol), K2CO3 (9.29 g, 67.35 mmol) and NMP (25 mL) were then charged. The reaction was heated to 130 C. and monitored by HPLC. The reaction was complete after 6 hours. The reaction was cooled to room temperature. DMC (11.4 mL, 134.69 mmol) and tetrabutylammonium bromide (TBAB) (0.868 g, 2.69 mmol) were added. The mixture heated to 130 C. HPLC showed less than 3% starting material remaining after 4.5 h. The mixture was filtered through a pad of diatomaceous earth. The black cake was washed with i-PrOAc (50 mL). Solution yield of this mixture was 78%. The crude product residue was dissolved in i-PrOAc (50 mL). The solution was washed with 0.3 N aqueous HCl three times (20 mL, then 2*15 mL). The organic phase was concentrated under vacuum. Propanol, water and 50% NaOH were added to the above residue. The reaction was heated to 90 C. for 1 h. HPLC showed that the reaction was complete. After the mixture was cooled to 50-60 C., diatomaceous earth and activated carbon were added. The mixture was stirred at 50 C. for 30 min and filtered to a 100 mL three neck flask through a pad of diatomaceous earth. The wet cake was washed with 18 mL of water/1-propanol 9/1. The mixture was then heated to 50 C. Acetic acid was added dropwise at this temperature. Precipitation was observed upon the addition. The suspension was then heated to reflux and held for 30 min. The mixture was slowly cooled to room temperature for 2 hours. The precipitate that formed was filtered. The wet cake was washed with 10 mL 1-propanol/water (2:1). The yellow solid was dried under vacuum for 2 days. 5.6 g product was obtained. The yield was 62% for three steps with 99.32 A % purity. 1H NMR (300 MHz, DMSO-d6) delta 8.80 (d, J=3.0 Hz, 1H), 8.14 (s, 1H), 8.00 (m, 1H), 7.77 (d, J=6.0 Hz, 1H), 7.69 (d, J=9.0 Hz, 1H), 7.59 (d, J=6.0 Hz, 1H), 7.50 (m, 1H), 3.89 (s, 3H), 3.70 (s, 3H), 3.17-3.11 (m, 1H), 1.90-1.60 (m, 8H).

The synthetic route of Methyl 3-amino-4-chlorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209465; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 17205-02-6,Some common heterocyclic compound, 17205-02-6, name is Ethyl 3-hydroxycyclobutanecarboxylate, molecular formula is C7H12O3, 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 ethyl 3-hydroxycyclobutanecarboxylate (10.2 g, 78.4 mmol) in dry pyridine (56.5 mL) at 0 C., TsCl (14.9 g, 78.4 mml) was added portion-wise. The resulting mixture was stirred at rt overnight. The reaction mixture was concentrated in vacuo and the residue obtained was dissolved in EtOAc (100 mL) and sequentially washed with 2 N HCl (100 mL), saturated NaHCO3 (100 mL) and water (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to obtain ethyl 3-(tosyloxy)cyclobutanecarboxylate as a pale yellow oil, which was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-hydroxycyclobutanecarboxylate, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica, NV; Player, Mark R.; Meegalla, Sanath K.; Illig, Carl R.; Chen, Jinsheng; Wilson, Kenneth J.; Lee, Yu-Kai; Parks, Daniel J.; Cheung, Wing S.; Huang, Hui; Patch, Raymond J.; US2014/364413; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 23877-12-5, The chemical industry reduces the impact on the environment during synthesis 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, I believe this compound will play a more active role in future production and life.

Reference Example 58 To a solution (50 ml) of (6-chloropyridin-3-yl)(2-hydroxy-4-methoxyphenyl)methanone (4.17 g) in N,N-dimethylformamide were added tert-butyl 2-bromo-2-methylpropanoate (17.6 g), potassium carbonate (10.9 g) and magnesium sulfate (5.70 g), and the mixture was stirred at 95C for 18 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, eluted with ethyl acetate-hexane (1:7, v/v) to give tert-butyl 2-{2-[(6-chloropyridin-3-yl)carbonyl]-5-methoxyphenoxy}-2-methylpropanoate as a colorless oil. Recrystallization from ethyl acetate-hexane gave colorless prism crystals (3.49 g, 54%). melting point 128 – 129C.

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, tert-Butyl 2-bromo-2-methylpropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1911738; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 110661-91-1, name is tert-Butyl 4-bromobutanoate, 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 110661-91-1, Formula: C8H15BrO2

a) A mixture of 3-chloro-4-hydroxy-5-methyl-benzonitrile (1 .15 g, 6.87 mmol) and Cs2C03 (13.43 g, 41.2 mmol) in DMF (45 ml.) is stirred at rt for 30 min before tert.-butyl 4- bromobutanoate (1 .55 g, 6.95 mmol) is added. The orange suspension is stirred at 65C for 72 h. Another portion of tert.-butyl 4-bromobutanoate (1 .55 g, 6.95 mmol) is added and stirring is continued at 65C for 24 h. The mixture is dilued with water (150 ml.) and extracted three times with DCM (3×50 ml.) and EA (3×50 ml_). The org. extracts are combined, dried over MgS04, filtered and concentrated. The crude product is purified by MPLC on silica gel eluting with heptane:EA:methanol to give tert-butyl 4-(2-chloro-4-cyano- 6-methylphenoxy)butanoate (645 mg) as a colourless oil; LC-MS: tR = 1 .01 min, [M+H]+ = no mass detectable; 1 H NMR (D6-DMSO): delta 7.94 (d, J = 1 .7 Hz, 1 H), 7.75 (d, J = 1.3 Hz, 1 H), 3.95 (t, J = 6.3 Hz, 2 H), 2.46 (t, J = 7.2 Hz, 2 H), 2.30 (s, 3 H), 1.98 (quint, J = 6.6 Hz, 2 H), 1 .41 (s, 9 H).

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; ACTELION PHARMACEUTICALS LTD; BOLLI, Martin; LESCOP, Cyrille; MATHYS, Boris; MORRISON, Keith; MUELLER, Claus; NAYLER, Oliver; STEINER, Beat; WO2012/98505; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 15441-07-3, 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. 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[0586] Preparation of 53 [0587] To a solution of 52 (0.08 g, 0.395 mmol) in CH2Cl2 (3 mL), added pyridine (74 muL) and methyl 3-(chlorosulfonyl)propanoate (0.1 g, 0.544 mmol). Reaction mixture was stirred for 16 h at rt. and then poured in 10% HCl solution followed by extraction with CH2Cl2. Organic layer was dried and evaporated to obtained 53 (52mg, 34%).

The synthetic route of Methyl 3-(chlorosulfonyl)propanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cambridge Enterprise Limited; Kapadnis, Prashant Bhimrao; Glen, Robert; Hiley, Robin; Bell, James; Spring, David; US2013/53372; (2013); 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 79669-50-4 as follows. SDS of cas: 79669-50-4

Compound BB-4A-2 (1.00 g, 4.37 mmol), compound BB-1A (1.40 g, 4.37 mmol) and potassium carbonate (1.81 g, 13.10 mmol) were dissolved in 1,4-dioxane (10 mL) and water (3 mL) under nitrogen atmosphere, followed by addition of (1,1′-bis(diphenylphosphino)ferrocene)palladium dichloride dichloromethane complex (356.50 mg, 436.55 mumol). The reaction mixture was stirred for 10 hours at 90 C under nitrogen atmosphere. After completion of the reaction, the reaction solution was cooled to room temperature and concentrated under reduced pressure, followed by addition of water (10 mL) and extraction with ethyl acetate (10 mL¡Á3). The organic phases were combined, washed with saturated brine (30 mL), dried over anhydrous sodium sulfate, filtered to remove the desiccant and concentrated under reduced pressure. The insoluble material was removed by filtration, and the obtained residue was purified by column chromatography (eluent: petroleum ether/ethyl acetate=100/1, 9/1) to obtain the title compound BB-4A-3 (yellow solid, 1.00 g, yield 59.74%). 1H NMR (400MHz,CDCl3) delta: 8.03 (d, J=2.0 Hz, 1H), 7.51 (dd, J=1.9, 7.9 Hz, 1H), 7.45 (d, J=8.8 Hz, 2H), 7.21 – 7.17 (m, 1H), 6.93 (d, J=8.8 Hz, 2H), 4.11 – 4.08 (m, 2H), 3.84 (s, 3H), 3.74 (t, J=4.9 Hz, 2H), 3.48 (t, J=6.7 Hz, 2H), 2.55 (s, 3H), 1.55 – 1.50 (m, 2H), 1.36 – 1.28 (m, 2H), 0.86 (t, J=7.4 Hz, 3H).

According to the analysis of related databases, 79669-50-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Medshine Discovery Inc.; LUO, Yunfu; BA, Yuyong; CHEN, Shuhui; (135 pag.)EP3567028; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6091-64-1, name is Ethyl 2-bromobenzoate, 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 6091-64-1, Quality Control of Ethyl 2-bromobenzoate

General procedure: Then, the corresponding ester was refluxed with 85% hydrazine monohydrate in ethanol to get hydrazide 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-bromobenzoate, and friends who are interested can also refer to it.

Reference:
Article; Li, Chao; Liu, Jia-Chun; Li, Ya-Ru; Gou, Cheng; Zhang, Mei-Ling; Liu, Hong-Yan; Li, Xiao-Zhen; Zheng, Chang-Ji; Piao, Hu-Ri; Bioorganic and Medicinal Chemistry Letters; vol. 25; 15; (2015); p. 3052 – 3056;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 52727-57-8,Some common heterocyclic compound, 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, molecular formula is C8H8BrNO2, 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.

(iii) Methyl 5-bromo-2-({[3-(furan-3-yl)phenoxy]acetyl}amino)benzoate Under ice-cooling, 1.53 g (7.97 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a DMAc (5 mL) solution comprising 1.45 g (6.64 mmol) of [3-(furan-3-yl)phenoxy]acetic acid, 1.60 g (6.97 mmol) of methyl 2-amino-5-bromobenzoate, and 1.08 g (7.97 mmol) of 1-hydroxybenzotriazole, and the mixture was stirred at room temperature for 4 hours. Under ice-cooling, 1.63 g (19.9 mmol) of 1-methylimidazole was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was stirred for 1 hour. The precipitates were collected by filtration and washed with water and IPE, followed by drying under reduced pressure at 50 C. for 3 hours, thereby giving 2.30 g of methyl 5-bromo-2-({[3-(furan-3-yl)phenoxy]acetyl}amino)benzoate (yield: 81%). 1H-NMR (CDCl3) delta: 3.97 (3H, s), 4.68 (2H, s), 6.72 (1H, dd, J=1.7, 1.0 Hz), 6.97 (1H, ddd, J=7.9, 2.6, 1.0 Hz), 7.19 (1H, ddd, J=7.9, 1.5, 1.0 Hz), 7.23 (1H, dd, J=2.6, 1.5 Hz), 7.35 (1H, t, J=7.9 Hz), 7.49 (1H, t, J=1.7 Hz), 7.67 (1H, dd, J=9.0, 2.4 Hz), 7.76 (1H, dd, J=1.4, 1.0 Hz), 8.19 (1H, d, J=2.4 Hz), 8.74 (1H, d, J=9.0 Hz), 12.08 (1H, s).

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-5-bromobenzoate, its application will become more common.

Reference:
Patent; RENASCIENCE CO., LTD.; US2012/22080; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 99548-54-6, 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. 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of methyl 3-bromo-2-methylbenzoate (500 mg, 3.3 mmol), NBS (770.4 mg, 4.3 mmol), and di-benzoyl peroxide (BPO, 80.7 mg, 0.3 mmol) in 1,2-dichloroethane (10 mL) was heated at 80 C for 12 h. The reaction mixture was cooled to room temperature, and the precipitated solid was removed by filtration and washed with ethers (10 mL). The filtrate was concentrated in vacuo and the residue was partitioned between 2 N NaHCO3 (15 mL) and ethers (15 mL). The organic layer was separated, dried over NaSO4, filtered and concentrated to give a crude product (683.2 mg, 89.6%), which was used in the next step reaction without further purification.

The chemical industry reduces the impact on the environment during synthesis Methyl 3-bromo-2-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Li, Qing; Meng, Liuwei; Zhou, Siru; Deng, Xiaoyan; Wang, Na; Ji, Yi; Peng, Yichun; Xing, Junhao; Yao, Gongmei; European Journal of Medicinal Chemistry; vol. 180; (2019); p. 509 – 523;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics