Category: 651780-27-7

Adding a certain compound to certain chemical reactions, such as: 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, 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 651780-27-7,651780-27-7

Toluene (40 mL) was added to a flask containing ethyl [6-BROM-1,] 2-benzisoxazole-3-carboxylate (3.15 g, 11.7 mmol), tetrakis (triphenylphosphine) palladium [(0)] (835 mg, 0.723 mmol, Strem), cesium carbonate (4.12 g, 12.6 mmol, Aldrich), and 2- (trifluoromethyl) phenylboronic acid (2. [38] g, 12.5 mmol, Aldrich) under argon. This mixture was heated in a 100 C oil bath for 35 hours. The mixture was diluted with EtOAc (250 mL) and washed with 4: 1 water: brine (250 [ML)] followed by brine (250 mL). The organics were filtered through a [1″PLUG] of silica gel and evaporated. Product was split in two, adsorbed onto silica gel, and purified on Biotage Flash 40 M+ silica cartridges using 20% EtOAc in heptane. Yield was 2.08 g of orange solid. [‘H] NMR (400 MHz, DMSO-d6) [5] ppm 1.42 (t, [J=7.] 15 Hz, 3 H) 4.51 (q, [J=7.] 05 Hz, 2 H) 7.52 (d, J=7. 46 Hz, [1] H) 7.51 (d, [J=8.] 09 Hz, 1 H) 7.71 (t, J=7. 57 Hz, [1] H) 7.79 (t, [J=7.] 36 Hz, 1 H) 7.91 (d, [J=7.] 67 Hz, [1] [H)] 7.93 (s, 1 H) 8.14 (d, J=8. 09 Hz, 1 H).

According to the analysis of related databases, 651780-27-7, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18428; (2004); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

651780-27-7,A common heterocyclic compound, 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, 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 solution of ethyl ^- fomo-l ,2-benzoxazole-3-caioxyiate (540.16 rag, 2 mmol, J .0 eq.) in THF ( iO mL) at -78 “C was added a solution of methyltnagncsiuja bromide in diethyl ether (3M, 3.33 HiL 10 mmol, 5.0 eq..). The resulting mixture was stirred at -78 C for 3 h. Sat. solo NH CI was added. The mixture was warmed to rt and extracted with EiOAc (3x). The combined extracts were washed with brine, dried over ajSO*, filtered and concentrated, under reduced pressure. The crude material was purified using normal phase flash chromatography on silica gel (0-50% EtOAc/hexanes) to provide die title compound (410 mg? 85.4% yield) as a white powder. H- MR (400 MHz, DMSO~<}: S 8.33 (s, IH), 8.06 (d, J=- 8.4 Hz, IH), 7,71 (dd, ,/ - 8.5, 1 A Hz, H), 2.73 (s 3H). The chemical industry reduces the impact on the environment during synthesis, 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate,I believe this compound will play a more active role in future production and life. Reference£º
Patent; VANDERBILT UNIVERSITY; CONN, P. Jeffrey; HOPKINS, Corey R.; LINDSLEY, Craig W.; NISWENDER, Colleen M.; ENGERS, Darren W.; PANARESE, Joe; BOLLINGER, Sean; ENGERS, Julie; (157 pag.)WO2016/115282; (2016); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

651780-27-7, 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.651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, it is a common compound, a new synthetic route is introduced below.

Step 3 6-(4-Hvdroxy-2-methyl-phenyl’)-benzordlisoxazole-3-carboxylic acid ethyl esterA solution of 3-methyl-4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenol (0.624 g, 2.67 mmol) and 6-bromo-benzo[d]isoxazole-3-carboxylic acid ethyl ester (0.360 g, 1.33 mmol) in 1,4-dioxane (20 mL) is added to a flask. The flask is evacuated and re-filled with N2 3 times. To this solution, Pd2(dba)3 (0.010 g), tricyclohexyl phosphine (10 mg), and aqueous K3PO4 (1.5 mL, 1.30 M) are added. The resulting mixture is heated to 50 C for 2 hours under N2. The reaction mixture is cooled to room temperature and filtered through a pad of diatomaceous earth. The filtrate is concentrated under reduced pressure. The residue is purified via silica gel chromatography eluting with 25% ethyl acetate in hexanes to give the title compound (0.366 g, 93%). ES/MS m/e 298.0 (M+l); 296.0 (M-I).

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. 651780-27-7, other downstream synthetic routes, hurry up and to see.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2007/92751; (2007); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – 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.651780-27-7,A new synthetic method of this compound is introduced below.651780-27-7

To a stirred solution of ethyl 6-bromo-1,2-benzoxazole-3-carboxylate (1.1 g) in THF (10 ml) and EtOH (3 ml), LiBH4 (0.133 g) was added drop wise at 0oC under inert atmosphere. The re- action mixture was stirred at 0oC for 2 h. Reaction was monitored by TLC. After the completion, the reaction mixture was diluted with Water (20 ml), quenched with 5% NaOH solution and ex- tracted with Ethyl acetate (30 ml x 2). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chro- matography (eluting in 15-20% ethyl acetate in heptane as a mobile phase) to afford (0.8 g) of the title compound. HPLC/MS (method 1): Rt : 1.587 min; MS: m / z = 229 (M+1).

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, Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate.

Reference£º
Patent; BASF SE; NARINE, Arun; ADISECHAN, Ashokkumar; VYAS, Devendra; DATTA, Gopal Krishna; VALLINAYAGAM, Ramakrishnan; CHAUDHURI, Rupsha; SAMBASIVAN, Sunderraman; (127 pag.)WO2018/177781; (2018); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

651780-27-7 A common heterocyclic compound, 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, 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.

20a) Ethyl 6-(4-hydroxyphenyl)-l,2-benzisoxazole-3-carboxylateEthyl 6-bromo-l,2-benzisoxazole-3-carboxylate (0.34 g, 1.26 mmol), (4- hydroxyphenyl)boronic acid (0.21, 1.51 mmol), tetrakis(triphenylphosphine)palladium (0) (0.06 g, 0.05 mmol) and 2 M sodium carbonate (5 mL) in 1 ,2-dimethoxyethane (6 mL) were stirred at 80 0C for 1 hour. The reaction mixture was diluted with water, followed by ethyl acetate. The layers were separated and the ethyl acetate layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to afford the crude material. The crude material was purified using hexanes: ethyl acetate (0 to 40% ethyl acetate) to afford a mixture of desired product, plus the free acid of the desired product, 6-(4-hydroxyphenyl)-l,2- benzisoxazole-3-carboxylic acid. All the fractions were combined and concentrated.

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 651780-27-7 reaction routes.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157270; (2008); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – 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 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, as follows.651780-27-7

20a) Ethyl 6-(4-hydroxyphenyl)-l,2-benzisoxazole-3-carboxylateEthyl 6-bromo-l,2-benzisoxazole-3-carboxylate (0.34 g, 1.26 mmol), (4- hydroxyphenyl)boronic acid (0.21, 1.51 mmol), tetrakis(triphenylphosphine)palladium (0) (0.06 g, 0.05 mmol) and 2 M sodium carbonate (5 mL) in 1 ,2-dimethoxyethane (6 mL) were stirred at 80 0C for 1 hour. The reaction mixture was diluted with water, followed by ethyl acetate. The layers were separated and the ethyl acetate layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to afford the crude material. The crude material was purified using hexanes: ethyl acetate (0 to 40% ethyl acetate) to afford a mixture of desired product, plus the free acid of the desired product, 6-(4-hydroxyphenyl)-l,2- benzisoxazole-3-carboxylic acid. All the fractions were combined and concentrated. The mixture was then dissolved in ethanol. Thionyl chloride was added, and the reaction mixture was reflux for 8 days. The reaction mixture was cooled to room temperature and concentrated. The concentrated material was diluted with 5% sodium bicarbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with water followed by brine, dried over magnesium sulfate, filtered, and concentrated. The crude material was purified using hexanes: ethyl acetate (0 to 100% ethyl acetate) to afford 0.044 g (13%) of ethyl 6-(4-hydroxyphenyl)- 1 ,2-benzisoxazole-3- carboxylate. 1H NMR (400 MHz, d6-DMSO): delta 9.76 (s, IH), 8.05 (m, 2H), 7.79 (dd, J = 8, 1 Hz, IH), 7.65 (d, J = 9 Hz, 2H), 6.88 (d, J = 9 Hz, 2H), 4.47 (q, J = 7 Hz, 2H), 1.39 (t, J = 7 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 651780-27-7, and friends who are interested can also refer to it.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157270; (2008); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

651780-27-7,A common heterocyclic compound, 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, 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.

10% Palladium on carbon (1.5 g) and triethylamine (7.5 g, 82.4 mmol) were added to a solution of ethyl 6-bromobenzisoxazole-3-carboxylate (20 g, 0.081 mol) in ethanol (300ml) at 0 C. under an atmosphere of nitrogen. The nitrogen atmosphere was removed by evacuation and replaced with hydrogen gas, and the reaction mixture was maintained for 1 hour. The hydrogen atmosphere was removed by evacuation and replaced with nitrogen gas, and the palladium removed by filtration through Celite. The filter cake was washed with ethanol (3¡Á50 mL) and the filtrates were concentrated. The residue was dissolved in dichloromethane (200 mL) and the solution was washed with water (4¡Á50 mL), dried (sodium sulfate) and evaporated to provide 13.0 g of the product as a yellow solid (96%). The ester was saponified using sodium hydroxide to provide the acid. The acid was coupled with the bicyclobase according to procedure A.

The chemical industry reduces the impact on the environment during synthesis, 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Xie, Wenge; Herbert, Brian; Ma, Jianguo; Nguyen, Truc Minh; Schumacher, Richard; Gauss, Carla Maria; Tehim, Ashok; US2005/250808; (2005); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

651780-27-7,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. Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate,651780-27-7, This compound has unique chemical properties. The synthetic route is as follows.

Diethyl malonate (12.6 g, 79 mmol) was added to a suspension of sodium hydride (3.16 g, 132 mmol) in dimethylsulfoxide (60 ml) over 30 min. The temperature of the reaction rose to 60 C and the mixture clarified. 1,4-Dibromo-2-nitrobenzene (10 g, 36.0 mmol) was added and the solution was maintained for 2 h at 100 C. The reaction mixture was allowed to cool to rt and was poured into ice (300g-400g). The precipitated solids were isolated by filtration and dried to provide 11.0 g of the product (89%). The ester (11.0 g, 32.0 mmol) was diluted with a 2 N solution of sodium hydroxide (32 mL, 63 mmol) and the reaction mixture was maintained at room temperature for 16 h. The aqueous layer was extracted with dichloromethane (20 mL) and was acidified. The precipitated solids were isolated by filtration and dried to provide 7.00 g of the acid (89%). Sulfuric acid (1 mL) was added to a solution of the acid (7.00 g, 27.0 mmol) in ethanol (60 ml). The reaction mixture was warmed to reflux, maintained for 2 h, and was concentrated under reduce pressure. The residue was partitioned between ethyl acetate (250 mL) and saturated sodium carbonate (50 mL) and the organic layer was washed with saturated sodium carbonate (50 mL) and brine (50 mL). The organic layer was dried (sodium sulfate) and concentrated to provide 8.00 g (98%) of the ester as a liquid. Under N2 atmosphere, sodium ethylate was formed with sodium (33.5 g, 1.46 mol) in ethanol (1.0 L). Isoamylnitrite (225 mL) was added to a solution of the ester (420 g, 1.46 mol) in ethanol (3 L) in a 10 L three-necked round bottom flask and the mixture was warmed to 60 C. A solution of sodium ethoxide, prepared from sodium metal (33.5 g, 1.46 mmol) in ethanol (1 L) was added dropwise and the reaction mixture was maintained for 2 h. The reaction mixture was allowed to cool to rt and was neutralized with 2 N hydrochloric acid. The reaction mixture was extracted with ethyl acetate (4 x 2L) and the combined organic layers were washed with water (2 x 1 L) and brine (2 x 1 L) and dried (sodium sulfate). The residue was purified by chromatography (1/1 to 0/1 hexane/ethyl acetate) to provide 110 g of the product ( 28%). 10% Palladium on carbon (1.5g) and triethylamine (7.5 g, 82.4 mmol) were added to a solution of ethyl 6-bromobenzisoxazole-3-carboxylate (20g, 0.081mol) in ethanol (300ml) at 0 C under an atmosphere of nitrogen. The nitrogen atmosphere was removed by evacuation and replaced with hydrogen gas, and the reaction mixture was maintained for 1 hour. The hydrogen atmosphere was removed by evacuation and replaced with nitrogen gas, and the palladium removed’by filtration through Celite. The filter cake was washed with ethanol (3 x 50 mL) and the filtrates were concentrated. The residue was- dissolved in dichloromethane (200 mL) and the solution was washed with water (4 x 50 mL), dried (sodium sulfate) and evaporated to provide 13.0 g of the product as a yellow solid (96%). The ester was saponified using sodium hydroxide to provide the acid. The acid was coupled with 1,4-diazabicyclo[3.2.2]nonane according to procedure A.

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, 651780-27-7.

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2005/111038; (2005); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – 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 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, as follows.651780-27-7

651780-27-7, Step 3 6-(4-Hvdroxy-2-methyl-phenyl’)-benzordlisoxazole-3-carboxylic acid ethyl esterA solution of 3-methyl-4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenol (0.624 g, 2.67 mmol) and 6-bromo-benzo[d]isoxazole-3-carboxylic acid ethyl ester (0.360 g, 1.33 mmol) in 1,4-dioxane (20 mL) is added to a flask. The flask is evacuated and re-filled with N2 3 times. To this solution, Pd2(dba)3 (0.010 g), tricyclohexyl phosphine (10 mg), and aqueous K3PO4 (1.5 mL, 1.30 M) are added. The resulting mixture is heated to 50 C for 2 hours under N2. The reaction mixture is cooled to room temperature and filtered through a pad of diatomaceous earth. The filtrate is concentrated under reduced pressure. The residue is purified via silica gel chromatography eluting with 25% ethyl acetate in hexanes to give the title compound (0.366 g, 93%). ES/MS m/e 298.0 (M+l); 296.0 (M-I).

According to the analysis of related databases, Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2007/92751; (2007); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

651780-27-7,A common heterocyclic compound, 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, 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.

10% Palladium on carbon (1.5g) and triethylamine (7.5 g, 82.4 mmol) were added to a solution of ethyl 6-bromobenzisoxazole-3-carboxylate (20g, 0. 081mol) in ethanol (300ml) at 0 C under an atmosphere of nitrogen. The nitrogen atmosphere was removed by evacuation and replaced with hydrogen gas, and the reaction mixture was maintained for 1 hour. The hydrogen atmosphere was removed by evacuation and replaced with nitrogen gas, and the palladium removed by filtration through Celite. The filter cake was washed with ethanol (3 x 50 mL) and the filtrates were concentrated. The residue was dissolved in dichloromethane (200 mL) and the solution was washed with water (4 x 50 mL), dried (sodium sulfate) and evaporated to provide 13.0 g of the product as a yellow solid (96%). The ester was saponified using sodium hydroxide to provide the acid. The acid was coupled with the bicyclobase according to procedure A. Literature reference: Angell, R. M.; Baldwin, I. R.; Bamborough, P.; Deboeck, N. M.; Longstaff, T.; Swanson, S. W004010995A1 The following acid was prepared using this method: 1,2-Benzisoxazole-3-carboxylic acid., 651780-27-7

The chemical industry reduces the impact on the environment during synthesis, 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2005/63767; (2005); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics