Tag: M.W=200-300

Synthetic Route of 110661-91-1,Some common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, molecular formula is C8H15BrO2, 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 suspension of ethyl 2-(4-chloro-2-hydroxyphenyl)acetate [CAS 1261826-30-5] (8.5 g, 39.6 mmol), C52CO3 (25.8 g, 79.2 mmol) in DMF (130 mL) at 10C was added dropwise tert-butyl 4-bromobutanoate [CAS 110611-91-1] (7 mL, 39.6 mmol). The mixture was stirred at room temperature overnight. The mixture wasdiluted with EtOAc and water. The layers were separated. The organic layer was washed with water, dried over MgSO4, filtered and the solvent was concentrated under reduced pressure. Purification was performed by flash chromatography on silica gel (15-40 pm, 120 g, heptane/EtOAc 90/1 0). The pure fractions were combined and concentrated to dryness to give tert-butyl 4-(5-chloro-2-(2-ethoxy-2-oxoethyl)phenoxy)butanoate 7a (12.7 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4-bromobutanoate, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; KESTELEYN, Bart Rudolf Romanie; BONFANTI, Jean-Francois; RABOISSON, Pierre Jean-Marie Bernard; MARCHAND, Arnaud Didier M; (64 pag.)WO2018/178238; (2018); A1;,
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Reference of 773873-95-3, 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. 773873-95-3, name is Methyl 2,2-difluorobenzo[d][1,3]dioxole-5-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step b: (2,2-Difluoro-benzo[1,3]dioxol-5-yl)-methanol Crude 2,2-difluoro-benzo[1,3]dioxole-5-carboxylic acid methyl ester (11.5 g) dissolved in 20 mL of anhydrous tetrahydrofuran (THF) was slowly added to a suspension of lithium aluminum hydride (4.10 g, 106 mmol) in anhydrous THF (100 mL) at 0 C. The mixture was then warmed to room temperature. After being stirred at room temperature for 1 hour, the reaction mixture was cooled to 0 C. and treated with water (4.1 g), followed by sodium hydroxide (10% aqueous solution, 4.1 mL). The resulting slurry was filtered and washed with THF. The combined filtrate was evaporated to dryness and the residue was purified by silica gel column chromatography to give (2,2-difluoro-benzo[1,3]dioxol-5-yl)-methanol (7.2 g, 76% over two steps) as a colorless oil.

The synthetic route of Methyl 2,2-difluorobenzo[d][1,3]dioxole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hadida Ruah, Sara S.; Miller, Mark T.; Bear, Brian; McCartney, Jason; Grootenhuis, Peter D. J.; US2008/9524; (2008); A1;,
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Synthetic Route of 6279-86-3, A common heterocyclic compound, 6279-86-3, name is Triethyl methanetricarboxylate, molecular formula is C10H16O6, 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 mixture of triethyl 1,1, 2-ethanetricarboxylate (3.51 mL, 15.30 mmol) and 2- (4-nitrophenyl)- ethanimidamide hydrochloride (46.95 g, 217.72 mmol) in anhydrous MeOH (300 mL) at room temperature was added NaOMe (3.8. 82 g, 718.49 mmol) and the resulting suspension was refluxed for 16 hours. After cooling to room temperature, the reaction mixture was chilled to 0C, acidified with 6N HCI, and the separated solids collected by suction and rinsed with cold water. Drying under high vacuum at 45C for 6 hours then gave methyl [4, 6-dihydroxy-2- (4-nitrobenzyl)- pyrimidin-5-yl] acetate (56.48 g, 81% yield) as a pale white powder.

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; BAYER HEALTHCARE AG; WO2005/73234; (2005); A2;,
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Related Products of 653-92-9, 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 653-92-9 as follows.

2-bromo-4-fluoro-1-nitrobenzene(185.16mg, 0.842mmol) to was added Pd 2 dba 3 (23.12mg, 0.025mmol) and copperpowder a (271mg, 4.26mmol). Dimethyl sulfoxide (2.3 ml) and methyl2-bromo-4-fluorobenzoate (0.122ml, 0.842mmol) was added and the mixture wasstirred vigorously for 2 hours at 100 C. The mixture was cooled to roomtemperature, diluted with ethyl acetate (20 ml), and filtered. The filtrate waswashed with water, dried (anhydrous Na 2 SO 4), and concentrated to give ayellow oil (279.8mg). It was used in the preparation of Example 38b withoutpurification this oil.

According to the analysis of related databases, 653-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; ENANTA PHARMACEUTICALS INCORPORATED; KU, YIYIN; MCDANIEL, KEITH F; CHEN, HUI-JU; SHANLEY, JASON P; KEMPF, DALE J; GRAMPOVNIK, DAVID J; SUN, YING; LIU, DONG; GAI, YONGHUA; OR, YAT SUN; WAGAW, SEBLE H; ENGSTROM, KEN; GRIEME, TIM; (87 pag.)JP5902123; (2016); B2;,
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These common heterocyclic compound, 17100-65-1, name is Methyl 2-bromo-4-methoxybenzoate, 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. Recommanded Product: 17100-65-1

To a reaction vial containing 7-amino-4-chloro-isoindolin-1-one (250 mg, 1.37 mmol) in dioxane (10 mL) was added methyl 2-bromo-5-methoxy-benzoate (502 mg, 2.05 mmol), cesium carbonate (893 mg, 2.74 mmol), copper iodide (104 mg, 0.55 mmol) and (1S,2S)-N1,N2-dimethylcyclohexane-1,2-diamine (156 mg, 1.1 mmol). The mixture was purged with nitrogen, then warmed to 110 C. The reaction was stirred at 110 C. for 1 h and the reaction was monitored by LC-MS. Following completion, the reaction was allowed to cool and was then filtered through Celite and rinsed with ethyl acetate. The crude was purified by silica gel chromatography (0-50% ethyl acetate/hexane) to give methyl 2-(7-amino-4-chloro-1-oxo-isoindolin-2-yl)-5-methoxy-benzoate. MS: (ES) m/z calculated for C17H15ClN2O4[M+H]+ 347.1, found 347.1.

The synthetic route of Methyl 2-bromo-4-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean R.; FAN, Junfa; KALISIAK, Jaroslaw; LELETI, Manmohan Reddy; MALATHONG, Viengkham; McMahon, Jeffrey; TANAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; Mali, Venkat; (62 pag.)US2017/144996; (2017); A1;,
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Application of 1150566-27-0, The chemical industry reduces the impact on the environment during synthesis 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, I believe this compound will play a more active role in future production and life.

To 3,3,3-trifluoropropan-1-ol (19 9 mmol) in DMSO was added NaH (19.9 mmol). The mixture was allowed to stir at room temp under inert atmosphere for 1 h. Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate (3.0 g, 13.3 mmol) was added and the reaction was warmed to 100 C until coupling was complete. After purification ethyl 6-(3,3,3-trifluoropropoxy)imidazo[1,2-b]pyridazine-3-carboxylate was obtained (1.2 g, 45%). MS (ESI) calcd for C12H12F3N3O3: 303.08

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; SIRTRIS PHARMACEUTICALS, INC.; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; WO2013/59587; (2013); A1;,
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Related Products of 69812-51-7, The chemical industry reduces the impact on the environment during synthesis 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of compounds 1a-1e or methyl 4-aminobenzoate (1.0 mmol) in pyridine (3.0 mL), the corresponding sulfonyl chloride (1.3 mmol) in pyridine (3.0 mL)were added dropwise under nitrogen atmosphere at 0 C, then the reaction mixture was stirred at room temperature overnight. The reaction was then acidified to pH=1 with 4NHCl(aq) and the resulting solid was collected by filtration. The crude product was purified by flash column chromatography (ethyl acetate-petroleum ether = 1:2) to give the title compounds 2a-2i.

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

Reference:
Article; Zhang, Jiankang; Shen, Luqing; Wang, Jincheng; Luo, Peihua; Hu, Yongzhou; Medicinal Chemistry; vol. 10; 1; (2014); p. 38 – 45;,
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Synthetic Route of 7459-46-3, 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. 7459-46-3, name is Triethyl ethane-1,1,2-tricarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of triethyl 1,1,2-ethanetricarboxylate (3.51 mL, 15.30 mmol) and 2-(4-nitrophenyl)ethanimidamidehydrochloride (46.95 g, 217.72 mmol) in anhydrous MeOH (300 mL) at r.t. was added NaOMe (3.8.82 g, 718.49 mmol)and the resulting suspension was refluxed for 16 h. After cooling to r.t., the reaction mixture was chilled to 0 C, acidifiedwith 6N HCl, and the separated solids collected by suction and rinsed with cold water. Drying under high vacuum at45 C for 6 h then gave methyl [4,6-dihydroxy-2-(4-nitrobenzyl)-5-pyrimidinyl]acetate (56.48 g, 81percent yield) as a palewhite powder.

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, Triethyl ethane-1,1,2-tricarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer HealthCare AG; EP1471057; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 2905-69-3,Some common heterocyclic compound, 2905-69-3, name is Methyl 2,5-dichlorobenzoate, molecular formula is C8H6Cl2O2, 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.

Example 4 Synthesis of 2-(2,5-Dichlorophenyl)-5-(pentafluorophenyl)-1,3,4-oxadiazole (10) Part A Synthesis of 2,5-Dichlorobenzohydrazide Into a flask was introduced 30 g (0.1463 mol) methyl 2,5-dichlorobenzoate and 46.89 g (1.463 mol) hydrazine. This was refluxed for 5 hours. The cooled reaction mixture was poured into an excess of water, to precipitate an off-white solid. Filtration and drying under vacuum gave 30 g solid. A 1H-NMR showed that the material was fairly pure 2,5-dichlorobenzohydrazide and was therefore used 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 Methyl 2,5-dichlorobenzoate, its application will become more common.

Reference:
Patent; 3M Innovative Properties Company; US7094902; (2006); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 39149-80-9, 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.

a) 1-(1-tert-Butoxycarbonyl-ethyl)-1H-pyrrole-2-carboxylic Acid Methyl Ester A 60% suspension of sodium hydride in mineral oil (0.704 g, 17.6 mmol) was added to anhydrous N,N-dimethylformamide (40 mL). 1H-Pyrrole-2-carboxylic acid methyl ester (2.0 g, 16 mmol) was dissolved in anhydrous N,N-dimethylformamide (8 mL) and added dropwise to the solution containing the sodium hydride over a period of 2 min. Effervescence was observed and the mixture was stirred for 30 min. 2-Bromo-propionic acid tert-butyl ester (4.0 g, 19.2 mmol) was added and the mixture was stirred at 80 C. for 45 min. Upon cooling to 25 C., the mixture was poured into 1.0 M aqueous hydrochloric acid solution (200 mL) and the product was extracted into ethyl acetate (200 mL). The organic phase was washed with saturated aqueous brine solution (50 mL), dried over magnesium sulfate and concentrated in vacuo. Purification by flash column chromatography (Merck silica gel 60, 40-63 muM, 10% ethyl acetate in hexanes) afforded the desired product, 1-(1-tert-butoxycarbonyl-ethyl)-1H-pyrrole-2-carboxylic acid methyl ester (3.8 g, 15 mmol, 94% yield) as clear oil. 1H NMR (400 MHz, CDCl3) delta: 1.45 (9H, s), 1.72 (3H, d, J=6.9 Hz), 3.79 (3H, s), 5.77 (1H, quartet, J=7.4 Hz), 6.18-6.20 (1H, m), 6.98-7.04 (2H, m).

The synthetic route of tert-Butyl 2-bromopropanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ruebsam, Frank; Dragovich, Peter; US2008/227774; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics