Tag: M.W:200-300

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

(2) Take 10.0g of intermediate (II) into a three-necked bottle.50ml ethanol, 4.8g iron powder,After refluxing for 0.5 h, 1 ml of sulfuric acid (6 mol/L) was added dropwise.After the completion of the dropwise addition, the reaction was refluxed for 1 h.After the reaction is completed, a NaOH solution is added to adjust the pH to 8,Cool down to 50 C, add 0.2g activated carbon,Reflux for 0.5h,Thermal filtration into the crystallization bottle, cooling and crystallization,Ethanol washing, drying to obtain intermediate (III) 9.60g, The yield is 95.1%.The melting point is 96.3-98.2 C.

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; Qilu Tianhe Huishi Pharmaceutical Co., Ltd.; Yuwen Li; Guan Qinghua; Zhao Xudong; Li Baoyong; (6 pag.)CN108250091; (2018); A;,
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 37924-85-9,3-(Bromomethyl)benzo[d]isoxazole, as follows.37924-85-9

General procedure: To NaOMe (25% soln, 0.5 mL, 2.2 mmol) in MeOH (5 mL) was added thiosemicarbazide 9 (200 mg, 2.2 mmol). Diethyloxalate (0.3 mL, 2.2 mmol) was then added dropwise. The mixture was heated at 65 C for 2 h and then cooled to rt. 1-(Bromomethyl)-4-chlorobenzene (500 mg, 2.4 mmol) was added in one portion; stirring was continued at rt for 3 h and then heated overnight at 50 C. The reaction mixture was concentrated. The residue was dissolved in EtOAc (40 mL), washed with water (20 mL), and brine (20 mL). The organic phase was dried over Na2SO4, concentrated and purified by silica gel column chromatography (EtOAc w/ 0.2% HOAc). The product was triturated in Et2O to afford 59 mg of 6g as a light yellow solid (10% yield)

According to the analysis of related databases, 3-(Bromomethyl)benzo[d]isoxazole, the application of this compound in the production field has become more and more popular.

Reference£º
Article; Hin, Niyada; Duvall, Bridget; Berry, James F.; Ferraris, Dana V.; Rais, Rana; Alt, Jesse; Rojas, Camilo; Slusher, Barbara S.; Tsukamoto, Takashi; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2088 – 2091;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

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

651780-27-7, A solution of ethyl 6-brom-1, 2-benzisoxazole-3-carboxylate (Intermediate 55) (0.05g) and cyclopropylamine (0. 03ml) in methanol (lml) was stirred at reflux for 6h. The solvent was evaporated and the residue was triturated with ether to give the title compound as a white solid (0.04g).

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; SMITHKLINE BEECHAM CORPORATION; WO2004/10995; (2004); 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.

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

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2005/111038; (2005); 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

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

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 37924-85-9,3-(Bromomethyl)benzo[d]isoxazole, as follows.37924-85-9

Step 1: To a -78 C solution of ((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[bl[1,4ldiazepin- 3-yl)-carbamic acid tert-butyl ester (807 mg, 2.91 mmol) in THF (19.4 mL) was added lithium bis(trimethylsilyl)amide (3.2 mL, 1.0 M solution in THF, 3.2 mmol), dropwise. The mixture was stirred at -78 C for 15 mm, then a mixture of Nal (523 mg, 3.49 mmol) and 3- (bromomethyl)benzo[dlisoxazole (740 mg, 3.49 mmol) in THF (9.7 mL) was added dropwise over 10 mm. The mixture was stirred at -78 C for 50 mm., warmed to RT and stirred for 4.5 h. The mixture was diluted with 1 N citric acid and extracted with EtOAc. The combined extractswere washed with sat. aq. NaHCO3, brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography. The resulting material was repurified by flash chromatography to provide a -4:1 mixture of (S)-tert-butyl 1-(benzo[dlisoxazol-3-ylmethyl)-2- oxo-2,3 ,4,5-tetrahydro- 1 H-benzo [bI [1 ,4jdiazepin-3-ylcarbamate and (S)-tert-butyl 1- (benzo [djisoxazol-3 -ylmethyl)-4-oxo-2,3 ,4,5 -tetrahydro- 1 H-benzo [bI [1,41 diazepin-3-ylcarbamate (742 mg, 63 %) as a yellow foam. LC-MS mlz 431 [M+Naj.Step 1: To a 0C solution of -4:1 mixture of tert-butyl (S)-1-((S)-1-(benzo[djisoxazol-3- ylmethyl)-2-oxo-2,3 ,4,5-tetrahydro- 1 H-benzo [bI [1,41 diazepin-3 -ylamino)- 1 -oxopropan-2- yl(methyl)carbamate and tert-butyl (S)-i -((S)-i -(benzo[dlisoxazol-3-ylmethyl)-4-oxo-2,3 ,4,5- tetrahydro- 1 H-benzo [bI [1 ,4ldiazepin-3-ylamino)- 1 -oxopropan-2-yl(methyl)carbamate (209.4 mg, 424 tmol) in CH2C12 (4.24 mL) was added pyridine (343 tL, 4.24 mmol), followed by methyl 4-(chlorocarbonyl)benzoate (92.7 mg, 467 tmol). After 1 h at 0 C the mixture was diluted with H20 and extracted with CH2C12. The combined extracts were washed with 1 N aq. citric acid, sat. aq. NaHCO3, and brine, dried over Na2504, filtered, and concentrated. The residue was purified by flash chromatography. The resulting material was repurified by flash chromatography to provide methyl 4-((S)-5-(benzo[djisoxazol-3 -ylmethyl)-3 -((S)-2-(tert-butoxycarbonyl(methyl)amino) propanamido)-4-oxo-2,3 ,4,5 -tetrahydro- 1 Hbenzo[b l[1,4ldiazepine-1-carbonyl)benzoate (194 mg, 70 %) as a white solid. LC-MS mlz 678 [M+Naj .

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

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHEN, Shaoqing; DONNELL, Andrew F.; KESTER, Robert Francis; LE, Kang; LOU, Yan; MICHOUD, Christophe; REMISZEWSKI, Stacy; RUPERT, Kenneth C.; WEISEL, Martin; WO2015/71393; (2015); 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 37924-85-9,3-(Bromomethyl)benzo[d]isoxazole, as follows.37924-85-9

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), 37924-85-9

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 3-(Bromomethyl)benzo[d]isoxazole, We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; BIOENERGENIX; MCCALL, John; KELLY, Robert, C.; ROMERO, Donna, L.; WO2014/66795; (2014); 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

Step 1: To a -78 C solution of ((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[bl[1,4ldiazepin- 3-yl)-carbamic acid tert-butyl ester (807 mg, 2.91 mmol) in THF (19.4 mL) was added lithium bis(trimethylsilyl)amide (3.2 mL, 1.0 M solution in THF, 3.2 mmol), dropwise. The mixture was stirred at -78 C for 15 mm, then a mixture of Nal (523 mg, 3.49 mmol) and 3- (bromomethyl)benzo[dlisoxazole (740 mg, 3.49 mmol) in THF (9.7 mL) was added dropwise over 10 mm. The mixture was stirred at -78 C for 50 mm., warmed to RT and stirred for 4.5 h. The mixture was diluted with 1 N citric acid and extracted with EtOAc. The combined extractswere washed with sat. aq. NaHCO3, brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography. The resulting material was repurified by flash chromatography to provide a -4:1 mixture of (S)-tert-butyl 1-(benzo[dlisoxazol-3-ylmethyl)-2- oxo-2,3 ,4,5-tetrahydro- 1 H-benzo [bI [1 ,4jdiazepin-3-ylcarbamate and (S)-tert-butyl 1- (benzo [djisoxazol-3 -ylmethyl)-4-oxo-2,3 ,4,5 -tetrahydro- 1 H-benzo [bI [1,41 diazepin-3-ylcarbamate (742 mg, 63 %) as a yellow foam. LC-MS mlz 431 [M+Naj.

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHEN, Shaoqing; DONNELL, Andrew F.; KESTER, Robert Francis; LE, Kang; LOU, Yan; MICHOUD, Christophe; REMISZEWSKI, Stacy; RUPERT, Kenneth C.; WEISEL, Martin; WO2015/71393; (2015); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

37924-85-9 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.

Step 1: To a -78 C solution of ((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[bl[1,4ldiazepin- 3-yl)-carbamic acid tert-butyl ester (807 mg, 2.91 mmol) in THF (19.4 mL) was added lithium bis(trimethylsilyl)amide (3.2 mL, 1.0 M solution in THF, 3.2 mmol), dropwise. The mixture was stirred at -78 C for 15 mm, then a mixture of Nal (523 mg, 3.49 mmol) and 3- (bromomethyl)benzo[dlisoxazole (740 mg, 3.49 mmol) in THF (9.7 mL) was added dropwise over 10 mm. The mixture was stirred at -78 C for 50 mm., warmed to RT and stirred for 4.5 h. The mixture was diluted with 1 N citric acid and extracted with EtOAc. The combined extractswere washed with sat. aq. NaHCO3, brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography. The resulting material was repurified by flash chromatography to provide a -4:1 mixture of (S)-tert-butyl 1-(benzo[dlisoxazol-3-ylmethyl)-2- oxo-2,3 ,4,5-tetrahydro- 1 H-benzo [bI [1 ,4jdiazepin-3-ylcarbamate and (S)-tert-butyl 1- (benzo [djisoxazol-3 -ylmethyl)-4-oxo-2,3 ,4,5 -tetrahydro- 1 H-benzo [bI [1,41 diazepin-3-ylcarbamate (742 mg, 63 %) as a yellow foam. LC-MS mlz 431 [M+Naj.

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 37924-85-9 reaction routes.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHEN, Shaoqing; DONNELL, Andrew F.; KESTER, Robert Francis; LE, Kang; LOU, Yan; MICHOUD, Christophe; REMISZEWSKI, Stacy; RUPERT, Kenneth C.; WEISEL, Martin; WO2015/71393; (2015); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

719-64-2,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. 5-Chloro-3-phenylbenzo[c]isoxazole,719-64-2, This compound has unique chemical properties. The synthetic route is as follows.

(3) According to a mass ratio of 30:2:0.08:1.7, methanol, 5-chloro-3-phenyl-2,1benzisoxazole, palladium-carbon catalyst, and ammonium formate were mixed and heated to reflux at 50C for 2 hours. After allowing to cool to room temperature, the mixture was filtered, and the resulting residue was vacuum dried at 50C for 4 hours to obtain 2-amino-5-chlorobenzophenone.

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, 719-64-2.

Reference£º
Patent; Shanxi Jujiehan Chemical Co., Ltd.; Li Changying; (5 pag.)CN107698453; (2018); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics