Tag: M.W=200-300

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. 39149-80-9, name is tert-Butyl 2-bromopropanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: tert-Butyl 2-bromopropanoate

To a suspension of sodium methanesulfinate (100 g; 929 mmol) in tBuOH (350 mL) was added tert-butyl-2-bromopropionate (150 mL; 877 mmol). The reaction mixture was stirred at about 90C for 24 h under nitrogen atmosphere, then cooled to rt and concentrated to dryness. The residue was partitioned between water (750 mL) and EA (600 mL). The aq. layer was extracted with EA (2 x 500 mL). The evaporation residue afford the title compound as a white yellow solid (175 g, 96% yield).1H NMR (d6-DMSO) delta 4.24 (q, J = 7.2 Hz, 1H); 3.1 1 (s, 3H); 1.45 (s, 9H); 1.40 (d, J = 7.2 Hz, 3H).

The synthetic route of 39149-80-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CHAPOUX, Gaelle; DIETHELM, Stefan; GAUVIN, Jean-Christophe; PANCHAUD, Philippe; SURIVET, Jean-Philippe; (90 pag.)WO2017/37039; (2017); 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. 685892-23-3, name is Methyl 2-bromo-6-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 2-bromo-6-chlorobenzoate

To a solution of methyl 2-bromo-6-chlorobenzoate (7.50 g, 30.1 mmol) in dioxane (65 mL) was added BPD (15.3 g, 60.3 mmol), AcOK (3.54 g, 36.1 mmol) and PdCl2(dppf) (0.66 g, 0.90 mmol) under N2 atmosphere, then the resulting mixture was stirred at 100 C. for 18 h, cooled to room temperature, filtered and concentrated, and the residue was purified by chromatography (0-3% EtOAc in petroleum ether) to give the title compound. MS: 297 (M+1). 1H NMR (400 MHz, CDCl3) delta 7.67 (d, J=7.4 Hz, 1H), 7.46 (d, J=7.8 Hz, 1H), 7.29-7.39 (m, 1H), 3.92 (s, 3H), 1.32 (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 685892-23-3.

Reference:
Patent; Merck Sharp & Dohme Corp.; Lapointe, Blair T.; Fuller, Peter H.; Gunaydin, Hakan; Liu, Kun; Molinari, Danielle F.; Pu, Qinglin; Scott, Mark E.; Trotter, B. Wesley; Zhang, Hongjun; US2018/305320; (2018); A1;,
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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 1236357-65-5 as follows. Product Details of 1236357-65-5

To degassed toluene (25 mL) was added palladium acetate (18 mg, 0.0825 mmol) and Xphos (79 mg, 0.165 mmol) and the mixture was degassed a further 30 minutes. To this reaction mixture was added methyl 1-(4-bromophenyl)cyclobutanecarboxylate (900 mg, 3.3 mmol) and cesium carbonate (3.2 g, 9.9 mmol) and this was degassed for a further 10 minutes. Beta-alanine ethyl ester (920 mg, 6.6 mmol) and diisopropylethyl amine (1.1 ml, 6.6 mmol) were added and this was brought to reflux and stirred overnight. The reaction was cooled to room temperature and poured onto water (100 ml). It was then extracted with ethyl acetate (2*100 ml), dried over magnesium sulfate, filtered, and evaporated to give methyl 1-(4-(3-ethoxy-3-oxopropylamino)phenyl)cyclobutanecarboxylate. Taken on crude to the next reaction. 1H NMR (400 MHz, CDCl3) 7.1 (d, 2H), 6.55 (d, 2H), 4.15 (m, 2H), 3.65 (s, 3H), 3.45 (m, 2H), 2.75 (m, 2H), 2.60 (t, 2H), 2.45 (m, 2H), 1.95 (m, 1H), 1.85 (m, 1H), 1.35 (m, 3H)

According to the analysis of related databases, 1236357-65-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; pfizer Inc; US2010/197591; (2010); A1;,
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Reference of 457097-93-7, A common heterocyclic compound, 457097-93-7, name is Methyl 4-amino-3-(trifluoromethoxy)benzoate, molecular formula is C9H8F3NO3, 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.

To a 500 mL round-bottom t1ask was added methyl4-amino-3-(trifluoromethoxy)5 benzoate (7.1 g, 30.19 mmoL 1.0 equiv.), AcOH (100 mL), and NaSCN (12.1 g, 149.25mmol, 5.0 equiv .), followed by the dropwise addition of a solution of bromine (9.6 g, 60.07mrnol, 2.0 equiv.) in AcOH (50 rnL) at 0 C over 1 hr. The mixture vvas stirred at 0 C for 2h, and then at 40 C overnight The reaction mixture vas cooled to 0 C, and a second batchofNaSCN (12.2 g, 150.49 mmol, 5.0 equiv.) was added, followed by the dropwise addition10 of a solution of bromine (9.6 g, 60.07 mmol, 2 0 equiv.) in AcOFf (50 mL) over l hr. Again,the reaction mixture was stirred at 0 C tor 2 h, and then at 40 C for 3 days. The resultingmixture was diluted Vith 200 mL of water and the pH value of the aqueous solution wasadjusted to 9 with sodium hydroxide. The resulting solids were collected by filtration,·washed ·with ·water (20 mL x 2), and dried in an oven at 60 C for 6 h to provide of rnethyl 2-15 amino-4-(trifluoromethoxy)-1 ,3-benzothiazole-6-carboxy late A-4b (54 g, 61 %) as a brornsolid.

The synthetic route of 457097-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
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Synthetic Route of 40876-98-0, These common heterocyclic compound, 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, 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 mixture of compound 1 (1 equiv) and aldehyde (1 equiv) together with an equimolar amount of amine in ethanol was refluxed towards completion (0.5 – 2 hours). Iced-water was added to the mixture after cooling and HCl was then added dropwise to pH 1. Filter the solid while appear. Traces aldehyde in the crude product was washed with water and ether to give (4a-k). Ethyl 4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate (4a) White solid; 60%; m.p. 106-109oC. IR (ATR) n/cm-1: 3344 (OH), 2986 (NH, amide), 1782 (C=O, ester), 1687 (C=C), 1670 (-N-C=O, amide), 1302 (C-N); 1H-NMR (400 MHz, CDCl3): delta 4.91-4.85 (2H, s, CH2), 4.39-4.32 (2H, q, J= 7.2 Hz, CH2), 1.38-1.31 (3H, t, J= 7.1 Hz, CH3); 13C-NMR (100 MHz, CDCl3,): delta 166.54 (COH), 164.23 (C=O) 151.29 (C=O), 116.09 (quat. C), 66.26 (OCH2), 62.09 (CH2), 14.34 (CH3); Anal. Calcd. for C7H9NO4: C, 49.12; H, 5.30; N, 8.18; O, 37.39. Found: C, 49.30; H, 4.65; N, 7.04; O, 39.01; GCMS m/z(EI, + ve): found 172.00 ([M]+), C7H9NO4 calculated 172.06

The synthetic route of 40876-98-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bacho, Muhamad Zulfaqar; Hamzah, Ahmad Sazali; Kamarulzaman, Firdaus; Mohammat, Mohd Fazli; Shaameri, Zurina; Wibowo, Agustono; Oriental Journal of Chemistry; vol. 36; 2; (2020); p. 309 – 319;,
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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. 24398-88-7, name is Ethyl 3-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H9BrO2

EXAMPLE 11. Synthesis of Ethyl 3-(5-Aminopyrimidin-2-ylamino)Benzoate(Intermediate 6); [0140] To a solution of 2-amino-5-nitropyrimidine (550 mg, 3.9 mmol) in 35 mL anhydrous 1,4-dioxane were added ethyl 3-bromobenzoate (1.8 g, 7.9 mmol), Xantphos, (230 mg, 0.4 mmol), Pd2(dba)3 (180 mg, 0.2 mmol) and Cs2CO3 (2.6 g, 8 mmol). The reaction mixture was stirred at 1000C for 5 h under argon. The solvent was removed under reduced pressure. The resulting solution was extracted with CHCl3 (3 x 50 mL) and saturated NaHCO3 (50 mL). The organic layer was separated, washed with brine, dried over Na2SO4 and filtered. The organic solvent was removed and the crude product was purified by silica gel column with CHCl3 as an eluent. The precipitated yellow solid was isolated by washed with chloroform and dried in vacuo (700 mg, 62%). 1H NMR (DMSO- de): delta 1.33 (t, J= 7.1 Hz, 3H), 4.33 (q, J = 7.1 Hz, 2H), 7.54 (t, J = 8.0 Hz, IH), 7.60-7.90 (m, IH), 7.95-8.10 (m, IH), 8.37 (t, J= 1.9 Hz, IH)3 9.26 (s, 2H)5 11.00 (s, IH).[0141] The above product was hydrogenated in 100 mL methanol/ethyl acetate (v/v: 1:1) using Pd/C (10%, 1 g) for 2 h. The palladium catalyst was removed by filtration, and the solvent was evaporated. The crude product was purified by silica gel column with 5% CH3OH / CHCl3 as an eluent to yield an off-white solid. MS (ES+): m/z 259 (M+H)+.

According to the analysis of related databases, 24398-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TARGEGEN, INC.; WO2008/8234; (2008); A1;,
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Reference of 139911-28-7,Some common heterocyclic compound, 139911-28-7, name is Ethyl 2-bromo-5-fluorobenzoate, molecular formula is C9H8BrFO2, 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.

Ethyl 2-(2-Methyl-4-fluorophenyl)-5-fluorobenzoate Tetrakis(triphenylphosphine)palladium(0) (0.02 eq, 0.31 g) was added to a vigorously stirred solution of ethyl 2-bromo-5-fluorobenzoate (1.0 eq, 3.3 g, 0.013 mol) and 2-methyl-4-fluorophenylboronic acid (1.2 eq, 0.016 mol, 2.4 g) in 45 mL of toluene, 22 mL of 2M aqueous sodium carbonate, and 11 mL of ethanol and the mixture was refluxed for 9 h. The cooled reaction mixture was poured into 50 mL each of water, ammonium hydroxide, and 2M aqueous sodium bicarbonate and then filtered through Celite. The filtrate was extracted with ethyl acetate and the organics were dried (MgSO4) and concentrated to yield 3.9 g of a yellow oil. Chromatography (silica gel, 20% ethyl acetate/hexane) gave 3.4 g (92%) of product as a light colored oil. 1 H NMR (CDCl3, 60 mHz) delta 7.7 (dd, 1 H), 7.5 (m, 1 H), 7.25- 6.75 (m, 4 H), 4.0 (q, 2 H), 2.0 (s, 3 H), 1.0 (t, 3 H); IR (CDCl3 solution) 3130, 2220, 1700, 1450, 1080 cm-1; MS m/z 276 (M+), 201 (base peak).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2-bromo-5-fluorobenzoate, its application will become more common.

Reference:
Patent; Alcon Laboratories, Inc.; US5070100; (1991); A;,
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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. 25542-62-5, name is Ethyl 6-bromohexanoate, A new synthetic method of this compound is introduced below., Safety of Ethyl 6-bromohexanoate

To a solution of triphenylphosphine (918 mg, 3.5 mmol) in MeCN (5 mL) was added 6-bromohexanoic acid ethyl ester (669 muL, 3.0 mmol). The mixture was refluxed for 7 h and concentrated. The residue was purified by silica gel column chromatography to give the target compound (1.14 g, 78%) as a white foam.1H NMR (500 MHz, CDCl3) delta: 7.89-7.85 (m, 6H), 7.81-7.78 (m, 3H), 7.72-7.68 (m, 6H), 4.07 (q, 2H, J = 7.3 Hz), 3.95-3.89 (m, 2H), 2.27 (t, 2H, J = 7.3 Hz), 1.76-1.72 (m, 2H), 1.66-1.58 (m, 4H), 1.22 (t, 3H, J = 7.3 Hz). FAB-MS m/z: 405 [M-Br]+.

The synthetic route of 25542-62-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Motoshima, Kazunori; Ishikawa, Minoru; Hashimoto, Yuichi; Sugita, Kazuyuki; Bioorganic and Medicinal Chemistry; vol. 19; 10; (2011); p. 3156 – 3172;,
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Related Products of 935273-86-2,Some common heterocyclic compound, 935273-86-2, name is Benzyl 3,3-difluorocyclobutanecarboxylate, molecular formula is C12H12F2O2, 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 benzyl 3,3-difluorocyclobutanecarboxylate (1.4 g, 6.2 mmol) in ethanol (50 mL) was added palladium on activated carbon (500 mg) and the reaction mixture was stirred at RT under an atmosphere of hydrogen (1 atm) for 12 h. The reaction mixture was filtered through a pad of CELITE and the filtrate was concentrated to afford Intermediate 291A as pale yellow liquid (550 mg, 65% yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 12.97-12.76 (m, 1H), 3.04-2.91 (m, 1H), 2.89-2.64 (m, 4H).

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

Reference:
Patent; Bristol-Myers Squibb Company; Velaparthi, Upender; Darne, Chetan Padmakar; Liu, Peiying; Wittman, Mark D.; Pearce, Bradley C.; Araujo, Erika M. V.; Dasgupta, Bireshwar; Nair, Jalathi Surendran; Janakiraman, Sakthi Kumaran; Rachamreddy, Chandrasekhar Reddy; Rao, Mettu Mallikarjuna; Karuppiah, Arul Mozhi Selvan Subbiah; Reddy, Bandreddy Subba; Nagalakshmi, Pulicharla; Bora, Rajesh Onkardas; Maheshwarappa, Shilpa Holehatti; Kumaravel, Selvakumar; Mullick, Dibakar; Sistla, Ramesh; (353 pag.)US9273058; (2016); B2;,
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Application of 252881-74-6, 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. 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Into a 10 liter glass reactor, 2080 g of a yellow oily liquid obtained in the above step and 4L of a 6 M hydrochloric acid solution were added. The reaction was carried out for 3 h at room temperature, and HPLC detection showed that the starting material had reacted completely. The reaction mixture was concentrated to dryness, neutralized with 1M sodium hydroxide solution to neutral, and concentrated again to dryness, samples were dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to give a colorless oil 1650g. HPLC analysis showed a product purity of 97% and a total reaction yield of 91%

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 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jiangsu Jinsirui Biological Technology Co., Ltd.; Shen Junwei; Zhang Fangliang; Zhang Jianqi; Luo Fulin; (11 pag.)CN109096128; (2018); A;,
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