Day: October 23, 2020

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

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 36216-80-5,Benzo[d]isoxazol-3-amine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.36216-80-5

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.

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, Benzo[d]isoxazol-3-amine.

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

Adding a certain compound to certain chemical reactions, such as: 239097-74-6,Benzo[d]isoxazol-5-amine, 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 239097-74-6,239097-74-6

Synthesis of N-benzofdlisoxazol-5-vl-2, 5-dichloro-benzenesulfonamide, STX 920 (KRB01048):; To a solution of 2, 5-dichlorobenzenesulphonyl chloride (192 mg, 0.783 mmol) in dichloromethane (4 mL) was added pyridine (150 uL, 1.86 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-1, 2-benzisoxazole (100 mg, 0.746 mmol) was added. The resulting mixture was stirred for 2 h at room temperature, then saturated NaHCO3 solution (10 mL) was added and the mixture was extracted into ethyl acetate (20 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a white solid (174 mg, 68%), single spot at Rf 0.68 (1: 1 hexane: ethyl acetate). mp 172.9- 173. 6C, HPLC purity 99+% (tR 2.41 min in 10% water-acetonitrile).’H NMR (CDCI3) : 5 8.64 (1H, s), 7.89 (1H, d, J=2.2 Hz), 7.56-7. 28 (5H, m). LCMS: 341.07 (M-). FAB-MS (MH+, C13H8Cl2N2O3S) : calcd 342.9711, found 342.9710.

According to the analysis of related databases, 239097-74-6, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; STERIX LIMITED; WO2005/42513; (2005); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

36216-80-5,The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a downstream synthesis route of the compound 36216-80-5

To a solution of triethylamine (0. 0025 mol) in CH2Cl2 (5 ml) benzoylchloride (0.0025 mol) was added. The mixture stirred at RT and intermediate 3 (0.0025 mol) in CH2C12 (5 ml) added dropwise. The reaction mixture was stirred overnight at RT. The mixture was washed 2 times with H20. The organic layer was separated, dried (MgS04), filtered off and the solvent was evaporated. The residue was purified by column chromatography over silicagel (eluent CH2Cl2) yielding O. OlOg compound 9 (yield of 2%, Melting Point 133C) and a fraction which was further purified by column chromatography over silicagel (eluent hexane/CH2Cl2) yielding 0.225 g of compound 10 (yield of 38%, Melting Point 97C-100C), and 0.100 g of compound 11 (yield of 17%, Melting Point 154C-160C)., 36216-80-5

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about Benzo[d]isoxazol-3-amine.

Reference£º
Patent; JANSSEN PHARMACEUTICA N.V.; WO2005/89753; (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 719-64-2,5-Chloro-3-phenylbenzo[c]isoxazole, as follows.719-64-2

(3) Mix tetrahydrofuran and triethylamine,Then add 5-chloro-3-phenyl-2,1 benzisoxazole,Palladium carbon catalyst mixing,Passing nitrogen,Replace the air 8 times,Then pass hydrogen to a pressure of 0.1 MPa.Magnetic stirring for 1h,Then filter,The obtained filter residue was vacuum dried at 50 C for 4 h.among them,Tetrahydrofuran,Triethylamine,5-chloro-3-phenyl-2,1 benzisoxazole,The mass ratio of the palladium carbon catalyst is 30:5:2:0.08,That is, 2-amino-5-chlorobenzophenone is obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-3-phenylbenzo[c]isoxazole, and friends who are interested can also refer to it.

Reference£º
Patent; SHAANXI JUJIEHAN CHEMICAL CO LTD; Shanxi Jujiehan Chemical Co., Ltd.; LI CHANGYING; Li Changying; (4 pag.)CN107827763; (2018); A;,
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

37924-85-9,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. 3-(Bromomethyl)benzo[d]isoxazole,37924-85-9, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of the above crude 3-(bromomethyl)benzo[d]isoxazole (15.3 g) in CH3CN (100 mL) was added a solution of KCN (4 g, 61 mmol) in water (19 mL). The resulting solution was stirred overnight at 40C, and then quenched with water (200 mL) and extracted with ethyl acetate (4 x 200 mL). The combined organic layers were washed with brine (2 x 100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford a residue, which was purified by a silica gelcolumn chromatography eluting with 1 % – 2% ethyl acetate in petroleum ether to afford 2-(benzo[d]isoxazol-3-yl)acetonitrile as a yellow solid (1.15 g, 15 ). LC/MS (ES, m/z): [M+H]+ 159.0 *H NMR (300 MHz, DMSO) delta 7.87 – 7.84 (d, / = 8.10 Hz, 1H), 7.66 – 7.61 (m, 2H), 7.47 – 7.40 (m, 1H), 4.13 (s, 2H)

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, 37924-85-9.

Reference£º
Patent; BIOENERGENIX; MCCALL, John; KELLY, Robert, C.; ROMERO, Donna, L.; WO2014/66795; (2014); 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 36216-80-5,Benzo[d]isoxazol-3-amine, as follows.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)., 36216-80-5

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Benzo[d]isoxazol-3-amine, and friends who are interested can also refer to it.

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

36216-80-5,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.

Example 4: (R)-l-(Benzo[rf]isoxazol-3-yIcarbamoylmethyl)-3-(l-phenyl- cycloheptanecarbonyloxy)-l-azonia-bicyclo[2.2.2]octane bromide To a mixture of benzo[Patent; ASTRAZENECA AB; ARGENTA DISCOVERY LIMITED; WO2009/138707; (2009); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 37924-85-9,3-(Bromomethyl)benzo[d]isoxazole, 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 37924-85-9,37924-85-9

BIOS-Na (Compound III) was prepared in accordance with the method described in Example 1 of U.S. Pat. No. 4,172,896. A solution of sodium sulfite (24.3 grams) in water (390 ml) was added to a solution of 3-bromomethyl-1,2-benzisoxazole (24 grams, Compound II) in methanol (390 ml), stirred with heating to 50 C. for 4 hours. After completion of the reaction, the solution was concentrated under reduced pressure. The resulting crystalline residue was heated to about 50-60 C. in methanol (750 ml) and the solution filtered. The clear filtrate was concentrated under reduced pressure and the resulting crystalline residue was washed with diethyl ether to give crystalline sodium 1,2-benzisoxazole-3-methanesulfonate (18 grams, BIOS-Na, Compound III). Thc thus-produced BIOS-Na was analyzed using X-Ray powder diffraction (results depicted in FIG. 1), differential scanning calorimetry (results depicted in FIG. 2) and thermal gravimetry (results depicted in FIG. 3). The water content of the thus-produced BIOS-Na was 7% as measured by Karl-Fischer titration, indicating that the crystals were of BIOS-Na monohydrate., 37924-85-9

According to the analysis of related databases, 37924-85-9, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; Naddaka, Vladimir; Adin, Itai; Klopfer, Eyal; Arad, Oded; Kaspi, Joseph; US2006/9644; (2006); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics