Month: May 2021

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. Recommanded Product: 40872-87-5

In one example of the inventive process, the reaction was conducted with methyl 3-amino-4-chloro-benzoate and 1-cyclopentyl-2-pyridinyl acetylene as the starting materials (Scheme 7). Suitable choices of ligand, base and solvent was important for obtaining satisfactory results as shown in Table 1. Several ligands were examined. It was found that the reaction proceeded smoothly to afford the desired indole product when using either ligand 4a, 4b or 5 in the presence of n-Bu4N+OAc-. The major side-reaction was homocoupling of the arylchloride via double amination (entries 1-3). The proper choice of base, solvent, temperature, and concentration was important to minimize the formation of the amination byproduct and also maximize the desired regioselectivity. By using inorganic bases such as K2CO3, a cleaner reaction could be obtained than by using n-Bu4N+OAc- as base. When a ferrocene ligand such as bis(diisopropylphosphino)ferrocene was employed, in combination with K2CO3 as base, the indolization of 2-chloroaniline with the internal acetylene completed rapidly, providing the product in high purity and regioselectivity (entry 4). Addition of LiCl or LiI as additive did not improve the yield. Instead, it slowed down the reaction (entries 5-6). With reduced catalyst loading (5 mol %), the reaction also proceeded smoothly and cleanly (entry 7). Changing the ratio of ligand to palladium acetate from 2:1 to 1:1 prolonged the reaction time (entry 8). Using K2CO3 as base, ligands 4a, 4b or 6 also afforded good results (entries 9-10). The wavelength used was 240 nm. TABLE I Base Time Entry (Scale) (eq) Catalyst (h) Result* 1 (100 mg) n-Pd(OAc)2 (10%) 4 Complete conversion of Bu4N+OAc- 2-(Di-t- starting material, giving 45 (2.5 eq) butylphosphino)- area % product and 33 biphenyl (40%) area % byproduct. 2 (100 mg) n-Pd(OAc)2 (10%) 3 Ratio of the desired product Bu4N+OAc- 1,1′- to starting material (2.5 eq) Bis(diphenylphosphino) (cholroaniline) was 5:1, ferrocene(20%) about 35 area % unknown impurities. The ratio of the regioisomers was 9:1. 3 (200 mg) n-Pd(OAc)2 (10%) 14 Complete conversion of the Bu4N+OAc- 1,1′-Bis(di-i- starting material, about 35 (2.5 eq) propylphosphino) area % of unknown ferrocene(20%) impurities. The ratio of the regioisomers was 9:1. 28% isolated yield was obtained through column chromatography for two steps. 4 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 3 Complete conversion of the 1,1′-Bis(di-i- starting material. The propylphosphino) desired product was formed ferrocene(20%) in 88 area % purity. The ratio of the regioisomers was 20:1. 5 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 Ratio of the desired product 1,1′-Bis(di-i- to the starting material was LiCl (1 eq) propylphosphino) 14:1. The ratio of the ferrocene(20%) regioisomers was 19:1. 6 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 The ratio of the desired 1,1′-Bis(di-i- product to the starting LiI (1 eq) propylphosphino) material was 1.6:1. ferrocene(20%) 7 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 5:1. The ratio ferrocene(10%) of regioisomers was 18:1. 8 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 2.5:1. The ferrocene(6%) ratio of regioisomers was 19:1. 9 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 Complete conversion of the 2-(Di-t- starting material, with about butylphosphino)- 20 area % impurities. The biphenyl (10%) ratio of the regioisomers was 20:1. 10 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired Tricyclohexylphosphine product to the starting (10%) material was 4:1. Ratio of the regioisomers was 18:1. *Ratios of product were measured by HPLC analysis

The synthetic route of 40872-87-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209465; (2005); A1;,
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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. 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 33689-29-1

Piperidine-1-carbonyl chloride (1.599 mL) was added to a solution of methyl 1-hydroxycyclopropanecarboxylate (1 mL) and DIEA (3.04 mL) in DCM (15 mL). The resulting solution was stirred at rt for 2 h, then diluted with DCM and the organic layer was wahed with iN HC1, water and brine, dried (Mg504), filtered andconcentrated. The residue was purified with silica gel gel to yield Cap L-7 Step a (0.75 g).

According to the analysis of related databases, 33689-29-1, the application of this compound in the production field has become more and more popular.

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;,
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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. 185629-32-7, name is Methyl 4-amino-3-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 4-amino-3-fluorobenzoate

4-Amino-3-fluorophenylhydrazide. Methyl 4-amino-3 -fluorob enzoate (250 mg, 1.48 mmols) was added to a 10 mL round bottom flask with stir bar, followed by addition of anhydrous hydrazine (500 1iL, 15.9 mmols). The reaction was then heated to 70C under N2 for 15 hours. After cooling, the mixture was poured into deionized water (40 mL), and the resulting precipitate was filtered and rinsed with additional water (50 mL) to give the product as a tan solid (130 mg, 52%). ?HNIVIR (400 MHz; DMSO-d6) = 9.41 (s, 1H), 7.48 (dd, J=12.8 Hz, 1.7 Hz, 1H), 7.43 (dd, J= 8.6, 1.7 Hz, 1H), 6.74 (t, J= 8.6 Hz, 1H), 5.66 (br, 2H),4.36 (br s, 2H). ?3C NIVIR (100 MFIz; DMSO-d6) 5= 165.4, 149.5 (d, J= 236.8 Hz), 139.5 (d,J 12.9 Hz), 124.0, 120.3 (d, J 4.8 Hz), 114.8 (d, J 3.9 Hz), 113.7 (d, J 19.6 Hz). ?9FNMR (376 IVIHz; DMSO-d6) = -136.96 (dd, J= 12.0, 9.2 Hz). Referenced againstCF3COOHat -76.55 ppm. (ESI) m/z calcd for C7H8FN3O (M) 169.0645, found 169.1001.

The synthetic route of 185629-32-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; RAIKHEL, Natasha, V.; HICKS, Glenn, R.; ZHANG, Chunhua; (107 pag.)WO2017/49016; (2017); A1;,
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Application of 35450-36-3, A common heterocyclic compound, 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, molecular formula is C9H9BrO3, 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.

General procedure: A sealed tube of 25 mL equipped with a magnetic stir bar was charged with alkynes (0.20 mmol), 2-bromobenzoic esters (0.22 mmol), CuI (0.02 mmol, 10 mol%), NaOH (0.4 mmol, 2 equiv) and CH3CN (1.0 mL). The reaction mixture was stirred at 100 C for 24 h. The reaction was monitored by GC or GC-MS. After completion of the reaction, the reaction mixture was cooled to room temperature, then washed with saturated NH4Cl aqueous solution (5.0 mL), and extracted with CHCl3 (3 * 5.0 mL). The combined organic phases were dried over Na2SO4 (anhydrous), concentrated in vacuum. The crude product was purified by flash column chromatography (eluent: ethyl acetate/petroleum ether = 1/20-1/10) on silica gel to afford the desired product.

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:
Article; Sun, Mengli; Su, Lebin; Dong, Jianyu; Liu, Long; Zhou, Yongbo; Yin, Shuang-Feng; Tetrahedron Letters; vol. 58; 25; (2017); p. 2433 – 2437;,
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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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of trans-Ethyl 4-hydroxycyclohexanecarboxylate

To a solution of ethyl 4-hydroxycyclohexanecarboxylate (5.00 g, 29.0 mmol) in dichloromethane (30 mL) was added 3,4-dihydro-2H-pyran (2.52 g, 29.0 mmol) and Amberlyst 15 (0.5 g). The reaction mixture was stirred at room temperature for 72 h, then another portion 3,4-dihydro-2H-pyran (1.89 g, 21.8 mmol) and Amberlyst 15 (0.5 g) was added, then after 5 h the reaction mixture was washed with sat. aq. sodium hydrogencarbonate solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to afford the title compound as a yellow oil (9 g), which was used directly in the next step.

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; Hoffmann-La Roche Inc.; Dehmlow, Henrietta; Martin, Rainer E.; Mattei, Patrizio; Obst Sander, Ulrike; Richter, Hans; US2013/109718; (2013); A1;,
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Reference of 3196-15-4, The chemical industry reduces the impact on the environment during synthesis 3196-15-4, name is Methyl 2-bromobutyrate, I believe this compound will play a more active role in future production and life.

5-Ethyl-2-pyrazin-2-yl-thiazol-4-ol: A solution of pyrazine-2-carbothioamide (1 g, 7.19 mmol) in ethanol (20 ml) was treated with methyl 2-bromobutyrate (1.56 g, 992 mul, 8.62 mmol) an pyridine (853 mg, 872 mul, 10.8 mmol) and heated to reflux for 2 hours. The reaction mixture was cooled and concentrated to dryness under reduced pressure, and the resulting solid was filtered and washed with diethyl ether to provide 5-ethyl-2-pyrazin-2-yl-thiazol-4-ol (0.740 g, 50%) which was used directly without further purification. MS (M+H)=208.

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

Reference:
Patent; Hoffmann-La Roche Inc; Bhagirath, Niala; Brameld, Kenneth Albert; Kennedy-Smith, Joshua; US2013/90334; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 37466-90-3, name is Ethyl 3,4-diaminobenzoate, 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 37466-90-3, name: Ethyl 3,4-diaminobenzoate

General procedure: Ethyl-3-amino-4-(2-substituted amino)benzoate, 3 (1 mmol) and various sodium bisulfite adducts, 4 (1.5 mmol) were dissolved in DMF (5 mL). The reaction mixture was stirred at 90 C under N2 atmosphere for 24-48 h. After completion of reaction (evident by TLC), the reaction mixture was diluted in ethyl acetate (25 mL) and washed with water (10 mL×3). The organic layer was collected, dried over Na2SO4 and evaporated under reduced pressure to afford crude products. Final compounds 5-7 were obtained in 38-90% yields after recrystallization from ethanol or column purification.

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:
Article; Yoon, Yeong Keng; Ali, Mohamed Ashraf; Wei, Ang Chee; Choon, Tan Soo; Ismail, Rusli; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 614 – 624;,
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Adding a certain compound to certain chemical reactions, such as: 619-45-4, name is Methyl 4-aminobenzoate, 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 619-45-4, Product Details of 619-45-4

To a stirred solution of compound I (1.51 g) in acetic acid Br2 (1.59 g) was added at 0 C. A large quantity of white solid was obtained. TCL result showed that no starting material remained. The solid was purified by column chromatography on silica gel (DCM:CH3OH = 20:1) to afford a white solid compound II (1.4g). The subsequent reaction followed the procedure outlined in Section 4.2.1.Total yield 0.7%, brownish yellow, 1H NMR (400 MHz, DMSO-d6): delta 7.034 (s, 3H), 7.731 (dd, J1 = 11.4 Hz, J2 = 1.60 Hz, 1H), 7.955 (d, J = 1.60 Hz, 1H), 8.647 (d, J = 8.80 Hz, 1H), 9.556 (s, 1H); 13C NMR (100 MHz, DMSO-d6): delta 179.38, 178.73, 159.26, 138.54, 128.52, 124.86, 123.93, 121.62, 116.51; HRMS (ESI) found: 345.9439, [C9H8N5S2BrO + H]+ calcd: 345.9432.

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

Reference:
Article; Sun, Ying; Wang, Wei; Sun, Yuanyuan; Han, Mei; European Journal of Medicinal Chemistry; vol. 46; 7; (2011); p. 2930 – 2936;,
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These common heterocyclic compound, 175278-29-2, name is Methyl 5-fluoro-2-methylbenzoate, 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. category: esters-buliding-blocks

A mixture of methyl 5-fluoro-2-methylbenzoate (0.5 g, 3.0 mmol),NBS (0.18 g, 3.0 mmol), and di-benzoyl peroxide (BPO) (36 mg, 0.15 mmol) in 1,2-dichloroethane (5 mL) was heated at 80 C for 12 huntil all starting material was consumed. The reaction 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 MgSO4, filtered and concentrated to give a crude product (0.65 g, 89%), which was used in the next step reaction without further purification.

The synthetic route of Methyl 5-fluoro-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Junli; Deng, Xiaoyan; Zhou, Siru; Wang, Na; Qin, Yujun; Meng, Liuwei; Li, Guobao; Xiong, Yuhua; Fan, Yating; Guo, Ling; Lan, Danni; Xing, Junhao; Jiang, Weizhe; Li, Qing; Bioorganic and Medicinal Chemistry; vol. 27; 4; (2019); p. 644 – 654;,
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Electric Literature of 69812-51-7,Some common heterocyclic compound, 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, molecular formula is C8H7ClO4S, 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: To an oven-dried Schlenk tube equipped with a magnetic stir bar was charged with tris(2,2′-bipyridyl)ruthenium(II) chloride (3 mol%), arenesulfonyl chloride (1.0 equiv.), heteroarene (1.0 equiv.), Na2CO3 (1.0 equiv.) and dry acetonitrile. The mixture was degassed by the freeze pump-thaw procedure, and then the Schlenk tube was irradiated under a 3W Blue LED bulb at a distance of 5 cm. After stirring at 25 C for 12 h, the solvent was removed under reduced pressure and the residue was then diluted with water. The aqueous solution was extracted (3 times) with ethyl acetate. The combined organic phases were dried over Na2SO4 and filtered. The filtrate was evaporated under reduced pressure to get the crude product, which was purified by column chromatography using hexane-ethyl acetate mixtures.

The synthetic route of 69812-51-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Natarajan, Palani; Bala, Anu; Mehta; Bhasin; Tetrahedron; vol. 72; 19; (2016); p. 2521 – 2526;,
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