Month: September 2021

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. 59247-47-1, name is tert-Butyl 4-bromobenzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of tert-Butyl 4-bromobenzoate

To a 100 mL round-bottom flask purged with and maintained under an inertatmosphere of nitrogen was added a solution of (1 S,4R,5R)-5-[[3-(2-chloro-6-t1uorophenyl)-5-cyclopropyl-L2-oxazol-4-yl]methoxy]-2-azabicyclo[2.2.1 ]heptan-3-one 306h (220 mg,0.58 mmol, 1.00 equiv.) in 1,4-dioxane (8 mL), tert-butyl4-bromobenzoate (180 mg, 0.7030 nm10l, 1.20 equiv.), Xantphos (51 mg, 0.09 mmol, 0.15 equiv), Pd2(dba)1 (27 mg, 0.03 mmol,0.05 equiv.), and Cs2C01 (286 mg, 0.88 mmol, 1.50 equiv.). The resulting mixture washeated at l05°C overnight After cooling to room temperature, the mixture was diluted with 50 mL ofvvater, and extracted with 200 mL of ethyl acetate. The organic extract was washedwith brine (lOO mL), dried over anhydrous sodiurn sulfate and concentrated lmder vacuum.The residue vas purified by silica gel column chromatography eluting with ethylacetate/petroleum ether (1 :4) to afford tert-buty 14-[(1 S,4R,5R)-5-[ [3-(2-chloro-6-5 t1uorophenyl)-5-cyclopropyl-l ,2-oxazol-4-yl]meihoxy ]-3-oxo-2-azabicyclo[2. 2.1 ]heptan-2-yl]benzoate 306c (250 mg, 77percent) as a yellow oil

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; 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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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 58656-98-7 as follows. COA of Formula: C11H13FO2

To the solution of tert-butyl 4-fluorobenzoate (500 mg, 2.55 mmol) and 3-hydroxybenzonitrile (306 mg, 2.55 mmol) in N,N-dimethylformamide (80 mL) was added potassium carbonate (528 mg, 3.8 mmol), the mixture was stirred at 130 C. for 1 hour under microwave. Then evaporated the solvent purified by column chromatography (silica gel, Petroleum ether/ethyl acetate=10:1) to give tert-butyl-4-(3-cyanophenoxy)benzoate (185 mg, 57%), as oil, 1H-NMR (300 MHz, CD3OD) delta 8.00 (m, 2H), 7.56 (m, 2H), 7.43 (m, 2H), 7.05 (m, 2H), 1.59 (s, 9H).

According to the analysis of related databases, 58656-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Constellation Pharmaceuticals, Inc.; Albrecht, Brian K.; Audia, James Edmund; Cook, Andrew S.; Gagnon, Alexandre; Harmange, Jean-Christophe; Nasveschuk, Christopher G.; US9206128; (2015); B2;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, 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 756525-95-8, Formula: C11H23NO4

Acetylenedicarboxylic acid (26.5 mg, 0.232 mmol, 1.0 eq.) was dissolved in NMP (1.0 mL) and cooled to 0 C, to which compound 159 (0.15 g, 0.557 mmol, 2.4 eq.) was added, followed by DMTMM (0.18 g, 0.65 mmol, 2.8 eq.) in portions. The reaction was stirred at 0 C for 5 h and then diluted with ethyl acetate and washed with water and brine. The organic solution was concentrated and purified by column chromatography (80-90% EA/PE). The appropriate fractions were concentrated and kept in refrigerator overnight. A solid formed and was filtered off. The filtrate was concentrated to give a light yellow oil (0.37 g, >100% yield), which was used without further purification. MS ESI m/z calcd for C26H45N2O10 [M+H]+ 545.30; found 545.30.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 9-Amino-4,7-dioxanonanoate, and friends who are interested can also refer to it.

Reference:
Patent; SUZHOU M-CONJ BIOTECH CO., LTD.; HANGZHOU DAC BIOTECH CO, LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; GAI, Shun; ZHAO, Linyao; YE, Hangbo; GUO, Huihui; TONG, qianqian; CAO, Minjun; JIA, Junxiang; YANG, Chengyu; LI, Wenjun; ZHOU, Xiaomai; XIE, Hongsheng; LIN, Chen; GUO, Zhixiang; YE, Zhicang; (246 pag.)WO2016/59622; (2016); A2;,
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Electric Literature of 1150566-27-0, 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. 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 7-(difluoromethyl)-6-(1-methyl-1H-pyrazol-4-yl)-1,2,3,4-10 tetrahydroquinoline (Intermediate C,700 mg,2. 67mmo ),ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate (600 mg,2.67 mmol)and K3P04 (1.69 g,7.98 mmol)in 2-methyl-2-butanol (10 mL)was added methanesulfonato(2-dicyclohexylphosphino-2′,4′,6′-tri-i-propyl-1,1’biphenyl)(2′-amino-1,1′-biphenyl-2-yl)palladium(II)(225 mg,0.27 mmol). The mixture washeated to 95 C for 12 h under an argon atmosphere. After cooling the reaction to room15 temperature,the mixture was filtered and concentrated in vacuo. The crude residue was purifiedby Prep-TLC (petroleum ether I EtOAc = 1 : 1)to give the title compound (110 mg,9%)asyellow oil. LCMS M/Z (M+H)453

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, Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; WAI, John; LAI, Kwong Wah; WANG, Fei; (251 pag.)WO2017/205536; (2017); A2;,
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Related Products of 34837-84-8,Some common heterocyclic compound, 34837-84-8, name is Methyl 2-(4-fluorophenyl)acetate, molecular formula is C9H9FO2, 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.

At 0C, to a suspension of NaH (6.7 g, 167.7 mmol) in THF (100 mL), a solution of methyl 2-(4-fluorophenyl)acetate (9.4 g, 55.9 mmol) and iodidemethane (23.8 g, 167.7 mmol) in THF (50 mL) was added drop wise. The resulting mixture was allowed to warmup to room temperature and stirred overnight. The residue was quenched with saturated aq. NH4CI and extracted with EtOAc. The organics were washed sequentially with water and brine, and dried over Na2SO4. Filtration and concentration in vacuum gave a crude product, which was purified by flash chromatography (silica gel, 0-30% EtOAc in PE) to afford the title compound (7.6 g, 69% yield). (ESI) mlz calcd for C11H13FO2: 196.09.Found: 197.17 (M+1).

The synthetic route of 34837-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DE LA ROSA, Martha Alicia; KAZMIERSKI, Wieslaw Mieczyslaw; (90 pag.)WO2019/3143; (2019); 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. 37466-90-3, name is Ethyl 3,4-diaminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

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.

The synthetic route of 37466-90-3 has been constantly updated, and we look forward to future research findings.

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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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. 685-88-1, name is Diethyl fluoromalonate, A new synthetic method of this compound is introduced below., Recommanded Product: 685-88-1

General procedure: Under argon atmosphere, n-butyllithium (0.10 mmol,20 mol%) in hexane (0.15 M, 0.67 mL) was added to a solutionof (R)-3,3-Cl2-BINOL (17.8 mg, 0.05 mmol, 10 mol%)in TBME (5.0 mL) at 0C. After stirring for 1 min, dibenzylmalonate (1a) (0.125 mL, 0.5 mmol, 1.0 eq) and diethyl maleate(2a) (0.096 mL, 0.6 mmol, 1.2 eq) was successively added tothe mixture at room temperature (r.t.). After 1 h, the reactionwas quenched with sat. NH4Cl aq. (2 mL) and stirred for 0.5 h.The aqueous layer was extracted with EtOAc (3 × 10 mL). Thecombined organic layers were washed with brine (20 mL),and dried over Na2SO4. After filtration and concentration, thecrude product was purified by column chromatography (hexane-EtOAc = 9 : 1, SiO2: 10 g) to give product 3aa as a colorless oil (214 mg, 94% yield, 90% ee)

The synthetic route of 685-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sakamoto, Midori; Kaneko, Tetsuya; Orito, Yuya; Shimoda, Yasushi; Nakajima, Makoto; Chemical and Pharmaceutical Bulletin; vol. 67; 5; (2019); p. 452 – 460;,
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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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H14O2

Example 226Atert-Butyl 1-[(4-chloro-3-nitrophenyl)(hydroxy)methyl]cyclopropanecarboxylate; 9.7 ml (24.3 mmol) of a 2.5 M solution of n-butyllithium in hexane were added dropwise to a solution, cooled to from -20 C. to -30 C., of 3.4 ml (24.3 mmol) of diisopropylamine in 20 ml of abs. THF. After the addition had ended, the mixture was stirred at from -20 C. to -30 C. for another 30 min. The mixture was then cooled to -78 C., and a solution of 2.53 g (17.8 mmol) of tert-butyl cyclopropanecarboxylate in 15 ml of abs. THF was added dropwise at this temperature. After 4 h at -78 C., a solution of 3 g (16.2 mmol) of 4-chloro-3-nitrobenzaldehyde in 15 ml of abs. THF was then added. The reaction mixture was slowly warmed to RT overnight and then allowed to stand at RT for three days, and saturated aqueous ammonium chloride solution was then added. The mixture was extracted with ethyl acetate and the organic phase was dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1?20:1). This gave 3.21 g of the target compound (60.6% of theory).LC-MS (Method 2): Rt=2.42 min; m/z=328 (M+H)+.1H-NMR (400 MHz, DMSO-d6): delta [ppm]=0.91-1.01 (m, 2H), 1.05-1.12 (m, 1H), 1.14-1.21 (m, 1H), 1.23 (s, 9H), 4.91 (d, 1H), 5.74 (d, 1H), 7.67-7.76 (m, 2H), 8.00 (d, 1H).

According to the analysis of related databases, 87661-20-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/172448; (2012); A1;,
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. 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate, A new synthetic method of this compound is introduced below., COA of Formula: C14H17NO4

General procedure: Anilinomethylenemalonates 8a-c (3 g, 10.83 mmol) were refluxed for 30 min in diphenyl ether (30 mL), leading to crude oxoquinolines 9a-c which were recrystallized from dimethylformamide [20,21,26,27].

The synthetic route of 54535-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Forezi, Luana Da S. M.; Tolentino, Nathalia M. C.; De Souza, Alessandra M. T.; Castro, Helena C.; Montenegro, Raquel C.; Dantas, Rafael F.; Oliveira, Maria E. I. M.; Silva Jr., Floriano P.; Barreto, Leilane H.; Burbano, Rommel M. R.; Abrahim-Vieira, Barbara; De Oliveira, Riethe; Ferreira, Vitor F.; Cunha, Anna C.; Boechat, Fernanda Da C. S.; De Souza, Maria Cecilia B. V.; Molecules; vol. 19; 5; (2014); p. 6651 – 6670;,
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Application of 14062-19-2, 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 14062-19-2 as follows.

To a solution of ethyl 4-methylphenylacetate (0.89 g, 5.o mmol) in dry methylene chloride (5 ml) cooled to -78 C. under nitrogen was added drop-wise 1.1 M di-isobutyl-aluminum hydride in toluene (4.5 ml, 5 mmol), keeping the internal temperature below -68 C. When the addition was complete, the reaction was quenched by drop-wise addition of methanol (5 ml), saturated potassium sodium tartrate solution (5 ml), and water (5 ml). The mixture was filtered through filter aid, the pad was washed with ethyl acetate (40 ml), and the filtrate layers were separated. The aqueous layer was extracted with ethyl acetate (40 ml). The combined ethyl acetate layers were washed with water (20 ml), and brine (20 ml), dried (sodium sulfate), filtered, and the solvent evaporated under reduced pressure to give 7.1 g of 4-methylphenylacetaldehyde as a volatile liquid: 1H NMR (CDCl3) 9.73 (1H, t, J 2.5 Hz), 7.17 (2H, m), 7.12 (2H, m), 3.64 (2H, d, J 2.5 Hz ), 2.35 (3H, s). To a stirred mixture of benzyl (trans-3-{[tert-butyl(dimethyl)silyl]oxy}cyclopentyl)carbamate (524 mg, 1.5 mmol), triethylsilane (0.36 ml, 260 mg, 2.25 mmol), and bismuth tribromide (45 mg, 0.10 mmol), in anhydrous acetonitrile (7.5 ml), was added the freshly prepared 4-methylphenylacetaldehyde (460 mg, approx. 2.2 mmol) slowly, keeping the temperature at or below 25 C. After stirring for 4 h, the reaction was quenched with half-saturated sodium bicarbonate (30 ml) and ethyl acetate (25 ml). The mixture was filtered through filter aid, the pad was washed with ethyl acetate (3×8 ml), and the filtrate layers were separated. The organic layer was washed with one-fifth saturated brine (8 ml) and water (8 ml), dried (sodium sulfate), filtered, and the solvent evaporated under reduced pressure to give a heterogeneous oil (1.19 g). The oil was chromatographed on silica gel, eluting with ethyl acetate:hexane (5:95 increasing to 25:75) to give a white solid. The solid was triturated with ethyl acetate:hexane (20:80), filtered off and dried to give benzyl {trans-3-[2-(4-methylphenyl)ethoxy]cyclopentyl}carbamate (291 mg, 55%) as a white solid. A second crop was obtained from the mother liquor (34 mg, 6%). 1H NMR (CDCl3) 7.35 (5H, m), 7.09 (4H, s), 5.08 (2H, s), 4.63 (1H, br s), 4.15 (1H, m), 3.95 (1H, m), 3.52 (2H, t, J 7 Hz), 2.84 (2H, t, J 7 Hz), 2.31 (3H, s), 2.12 (2H, m), 1.92 (1H, m), 1.68 (1H, m), 1.58 (1H, m), 1.36 (1H, m).

According to the analysis of related databases, 14062-19-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Thompson, Wayne; Young, Steven D.; Phillips, Brian T.; Munson, Peter; Whitter, Willie; Liverton, Nigel; Dieckhaus, Christine; Butcher, John; McCauley, John A.; McIntyre, Charles J.; Layton, Mark E.; Sanderson, Philip E.; US2005/54658; (2005); A1;,
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