Category: Benzisoxazole

Name is 3-(Bromomethyl)benzo[d]isoxazole, as a common heterocyclic compound, it belongs to Benzisoxazole compound, and cas is 37924-85-9, its synthesis route is as follows.

(b) A solution containing 1-dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)-imidazole (6.7 g, 0.025 mole), and 3-bromomethyl-1,2-benzisoxazole (5.3 g, 0.025 mole) in anhydrous acetonitrile (30 mL) is stirred at reflux for 72 hours. The reaction mixture is cooled and mixed with a solution of sodium methoxide (3 g, 0.055 mole) in methanol (30 mL). The resulting solution is stirred at reflux for 26 hours. The solvents are evaporated and the residue is taken up in 1N hydrochloric acid (30 mL). This solution is allowed to stand at ambient temperature for 3 hours and is then made basic (pH 9) by addition of 50% aqueous sodium hydroxide solution. The mixture is extracted with methylene chloride (2*25 mL) and the combined extracts are washed with water (2*20 mL), dried over anhydrous sodium sulfate, filtered, and the solvent is evaporated to give crude 3-[(5-(3-hydroxypropyl)-1H-imidazol-1-yl)methyl]-1,2-benzisoxazole which is purified by trituration with acetone (15 mL), m.p. 129-131 C.

37924-85-9, 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.,37924-85-9 ,3-(Bromomethyl)benzo[d]isoxazole, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; Ciba-Geigy Corporation; US4859691; (1989); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

36216-80-5, 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. Benzo[d]isoxazol-3-amine, cas is 36216-80-5,the Benzisoxazole compound, it is a common compound, a new synthetic route is introduced below.

A mixture of benzo[d]isoxazol-3-ylamine (3.0 g) and CICO2Ph (0.94 ml_) in dry CH3CN (30 ml_) was stirred for 23 h at 70 0C. The reaction mixture was poured into de- ionized water, stirred for 30 min and filtered. The isolated solid was rinsed thoroughly with water and then dried under high vacuum to give 1.90 g (100%) of the title compound. MS: 255.1.

The chemical industry reduces the impact on the environment during synthesis,36216-80-5,Benzo[d]isoxazol-3-amine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/153752; (2008); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

Name is Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, as a common heterocyclic compound, it belongs to Benzisoxazole compound, and cas is 651780-27-7, its synthesis route is as follows.

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.

651780-27-7, 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 ,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, other downstream synthetic routes, hurry up and to see

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

36216-80-5, 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. Benzo[d]isoxazol-3-amine, cas is 36216-80-5,the Benzisoxazole compound, it is a common compound, a new synthetic route is introduced below.

To a solution of benzo[d]isoxazol-3-amine (1 eq.) and quinuclidin-3-one (1.1 eq.) in toluene (7 mL/mmol benzo[d]isoxazol-3-amine) at 25 C was added portion-wise titanium(IV) isopropoxide (9 eq.). The resulting solution was stirred at 100 C for 12 hours. On completion, the mixture was cooled to 0 C, and ethanol (1 mL/mmol benzo[d]isoxazol-3-amine) was added via syringe, followed by sodium borohydride (3.7 eq.) in portions. The reaction was stirred at 25 C for 3 hours, then quenched with saturated aqueous potassium carbonate solution, resulting in the formation of a solid. The mixture was filtered, and the filtrate was extracted with dichloromethane (5 chi 50 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The filter cake from the original filtration was slurried with methanol, and the mixture was filtered. The filtrate was directly evaporated to dryness. The combined residue from both batches was dissolved in 4N hydrochloric acid (20 mL) and stirred at room temperature for 4 hours. The mixture was made basic by addition of saturated potassium carbonate solution and extracted with dichloromethane (5 x 50 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by prep-HPLC to give the racemic aminobenzoisoxazole product. [00408] Chiral Separation: A solution of racemic aminobenzoisoxazole product in 3-5 mL of methanol was separated by cSFC (Waters SFC Prep 80, Column temperature: 25 C, back pressure: 100 bar, and wavelength: 220 nm). Each set of collected fractions was concentrated at room temperature. The residue was dissolved in 0.2 M hydrochloric acid and lyophilized to give each enantiomer of the aminobenzoisoxazole product; Following general procedure Bl, rac-1 was prepared from benzo[d]isoxazol-3 -amine (0.40 g, 3.0 mmol). The product was purified by prep-HPLC [Instrument: GX-A; Column: Phenomenex Gemini C18 150×25 mm, particle size: 10 mupiiota; Mobile phase: 44-74% acetonitrile in H20 (add 0.5% NH3 H20, v/v)] to give rac-1 (70 mg, 9% yield) as a yellow solid. LCMS (B): tPv=1.179 min., (ES+) m/z (M+H)+ = 244.2.

The chemical industry reduces the impact on the environment during synthesis,36216-80-5,Benzo[d]isoxazol-3-amine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; MCRINER, Andrew, J.; (127 pag.)WO2016/201096; (2016); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, 719-64-2,5-Chloro-3-phenylbenzo[c]isoxazole, 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. 719-64-2

719-64-2, (3) 5-Chloro-3-phenyl-2,1 benzisoxazole,Iron powder,The concentration of 95% ethanol,Heat reflux at 35C for 30 minutes,Then, ethanol was added dropwise to the system.among them,The volume ratio of hydrochloric acid to ethanol is 1:5.After refluxing, reflux at 35C for 2 hours.Sodium hydroxide solution was added dropwise to adjust the pH of the system to 7,Add activated carbon to the systemContinue refluxing for 20 minutes,filter,The filter residue is vacuum dried at 50C for 4 hours.among them,5-chloro-3-phenyl-2,1benzoxazole,Iron powder,95% ethanol,Ethanol solution of hydrochloric acid,The mass ratio of activated carbon is 2:1.2:15:2:0.2,That is, 2-amino-5-chlorobenzophenone is obtained.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5-Chloro-3-phenylbenzo[c]isoxazole,719-64-2,its application will become more common.

Reference£º
Patent; Shanxi Jujiehan Chemical Co., Ltd.; Li Changying; (5 pag.)CN107698454; (2018); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, 37924-85-9,3-(Bromomethyl)benzo[d]isoxazole, 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. 37924-85-9

(b) Sodium hydride (50% in mineral oil, 3.4 g, 0.071 mole) is washed free of mineral oil with hexane (3*30 mL) and suspended in dimethylformamide (100 mL). This suspension is well stirred and maintained near room temperature (water bath) during the dropwise addition of a solution of imidazole (4.8 g, 0.071 mole) in dimethylformamide (25 mL). The reaction mixture is stirred at room temperature for 1 hour when 3-bromomethyl-1,2-benzisoxazole (15.0 g, 0.071 mole) is added all at once. The mixture is then heated at 85 C. for 8 hours. The solvent is evaporated in vacuo and the residue is taken up in methylene chloride (200 mL) and washed with water (3*50 mL). The organic solution is dried over anhydrous sodium sulfate, filtered and evaporated to give 3-[(1H-imidazol-1-yl)methyl]-1,2-benzisoxazole, which is purified by recrystallisation from isopropanol, m.p. 52-55 C.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3-(Bromomethyl)benzo[d]isoxazole,37924-85-9,its application will become more common.

Reference£º
Patent; Ciba-Geigy Corporation; US4859691; (1989); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, 36216-80-5,Benzo[d]isoxazol-3-amine, 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. 36216-80-5

Example 24; N-1,2-Benzisoxazol-3-yl-1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperidine-4-carboxamide; [Show Image] To a solution of 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperidine-4-carboxylic acid (289 mg, 1.00 mmol) and N,N-dimethylformamide (0.010 ml) in tetrahydrofuran (5 ml) was added in water-bath, oxalyl chloride (0.174 ml, 2.00 mmol), and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure. The residue was added to a solution of 1,2-benzisoxazol-3-amine (134 mg, 1.00 mmol) in pyridine (0.404 ml, 5.00 mmol) under ice-cooling, followed by stirring at room temperature for 1 hour. The solvent was distilled off under reduced pressure. The residue was poured to water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane : ethyl acetate = 1 : 1) to give the desired product as a solid. The resulting solid was recrystallized from a mixed solvent of hexane and ethyl acetate to give 60.3 mg (14.9%) of the desired product. 1H-NMR (CDCl3) delta; 2.05 – 2.22 (4H, m), 2.88 (1H, br s), 3.36 – 3.45 (2H, m), 4.11 – 4.18 (2H, m), 7.32 – 7.63 (6H, m), 8.19 – 8.27 (3H, m), 9.46 (1H, br s).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,Benzo[d]isoxazol-3-amine,36216-80-5,its application will become more common.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP1813606; (2007); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, 16263-54-0,3,6-Dichlorobenzo[d]isoxazole, 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. 16263-54-0

3,6-dichlorobenzisoxazole (5.2 g, 27.8 mmol) and piperazine anhydride (24 g, 278 mmol) were placed in an eggplant type flask and reacted at 120 C. for 24 hours. After completion of the reaction, 52 ml of ice water was added to quench , Add 15 ml of 50% NaOH solution to the solution, stir for 5 minutes, extract with 30 ml * 3 dichloromethane, combine dichloromethane layer, wash with saturated brine 20 ml, dehydrate with anhydrous MgSO 4, evaporate to dryness, Isolated by alumina (200-300 mesh) column chromatography eluting with dichloromethane: methanol = 100: 1 to obtain 4.7 g of 6-chloro-3-piperazinyl-benzisoxazole, Yield is 71%.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16263-54-0,3,6-Dichlorobenzo[d]isoxazole,its application will become more common.

Reference£º
Patent; JIANGSU HENGYI PHARMACEUTICAL COMPANY LIMITED; SHANGHAI INSTITUTE OF PHARMACEUTICAL INDUSTRY; Li, JIANQI; PENG, SHAOPING; CAI, WANGPING; GAO, KAI; (39 pag.)JP5714152; (2015); B2;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, 36216-80-5,Benzo[d]isoxazol-3-amine, 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. 36216-80-5

(2) Bis(2,2,2-trichloroethyl) 1,2-benzisoxazol-3-ylimidodicarbonate; To a solution of 1,2-benzisoxazol-3-amine (4.00 g, 29.8 mmol) and pyridine (7.25 ml, 89.6 mmol) in tetrahydrofuran (100 ml) was added under ice-cooling, 2,2,2-trichloroethyl chloroformate (8.20 ml, 59.6 mmol), and the mixture was stirred under ice-cooling for 1 hour and at room temperature for 20 minutes. The reaction mixture was poured to water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. To the residue was added hexane to give 13.3 g (91.7%) of the desired product as a solid. 1H-NMR (CDCl3) delta; 4.82 (4H, s), 7.36 – 7.44 (1H, m), 7.59 – 7.65 (3H, m).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,36216-80-5,Benzo[d]isoxazol-3-amine,its application will become more common.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP1813606; (2007); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

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. 651780-27-7

A mixture of ethyl 6-bromobenzoisoxazole-3-carboxylate (550 mg, 1.39 mmol), o- tolylboronic acid (377 mg, 1.5 [EQ),] Pd (PPh3) 4 (171 mg, 0.08 [EQ),] toluene (10 mL), ethanol (1.5 mL), and 1 M [NA2C03] (1.5 [ML)] is stirred at reflux for 3.5 h. The reaction mixture is diluted with [CHUCK] (0.1 L) and [H2O] (0.1 mL). The [CHZC12] solution is dried [(NA2S04),] filtered, and evaporated. The residue is purified by silica chromatography (heptane/EtOAc) to give Preparation [PA.’H] NMR (300 MHz, CDC) 8 8.14 (1H), 7.61 (2H), 7.42 (1H), 7.35-7. 2 (1H), 4.59 (2H), 2.28 (3H), 1.51 (3H).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate,its application will become more common.

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