Category: Benzisoxazole

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

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.

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

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2005/63767; (2005); A2;,
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

1 ,2-Benzoxazol-3-amine (802 mg, 5.98 mmol) was dissolved in a mixture of anhydrous dichloromethane (4 ml_) and anhydrous pyridine (1 .5 ml_, 19 mmol). To this mixture was added, drop-wise, a solution of ethyl malonyl chloride (1.00 g, 6.64 mmol) in anhydrous dichloromethane (4 ml_). The resulting warm mixture (from slight exotherm) was stirred at ambient temperature for 30 min and quenched with the addition of cold water (20 ml_). Solid sodium carbonate was added until a pH of 10 was reached, and the mixture was stirred at ambient temperature for 1 hour. The organic layer was separated and the aqueous layer back-extracted withdichloromethane (4 x 30 ml_). The combined organic layers were passed through a phase separator column and concentrated under reduced pressured to yield crude ethyl 3-(1 ,2-benzoxazol-3-ylamino)-3- oxopropanoate., 36216-80-5

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; TARGACEPT, INC.; MAZUROV, Anatoly A.; MIAO, Lan; SHOWALTER, Todd; WO2013/28587; (2013); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, 239097-74-6,Benzo[d]isoxazol-5-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. 239097-74-6

To a suspension of intermediate ester (105 mg, 0.340 mmol) in DMF (0.5 mL) was added a solution of 1,2-benoxazol-5-amine (46 mg, 0.340 mmol) in DMF (0.5 mL). The reaction mixture was stirred at room temperature for 2 hours until the reaction was complete, and quenched with the addition of TFA (5 drops). The precipitated solid was collected by filtration, suspended in DCM, basified with saturated NaHCO3 to pH ~8. The aqueous layer was extracted with DCM, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by trituration in DCM/Et2O, collected by filtration, and dried in vacuo to give the title compound (50 mg, 48%) as a yellow solid.1H NMR (400 MHz, CDCl3): delta 10.05 (s, 1H), 8.72 (s, 1H), 8.55 (s, 1H), 8.07 (s, 1H), 7.68 (dd, J = 6.8 Hz, 1.6 Hz, 1H), 7.59 (d, J = 6.8 Hz, 1H), 6.59 (s, 1H), 2.71 (s, 3H), 2.70 (s, 3H). LC-MS m/z: 308.1 [M+H+]. HPLC Purity (214 nm): 98%; tR = 8.38 min.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,239097-74-6,Benzo[d]isoxazol-5-amine,its application will become more common.

Reference£º
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse Marie, Josee; (134 pag.)WO2016/73889; (2016); 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

(21). Iris{dibenzylideneacetoae)dipailadiuffi (123.6 mg, 0.14 mmol, 9.0 MO1%), XantPhos ( 104 mg, 0. 8 mmo’l. 12 moi%), ethyl 6-bromobenzo|d]isoxazole-3-carboxylate (608 mg, 2.25 mmol, 1.5 eq.),l- jX4 raemoxypheny1)me&yI}pyjrazofo^^(381 mg, 1.5 mmol, 1.0 eq.) and cesium carbonate (731 rag, 2.25 mmol. 1 ,5 eq.) were charged in a microwave vial. The vial was evacuated and purged with nitrogen (3X) and 1,4-dioxane (7.5 mL) was added. The reaction mixture was subjected to a microwave reactor tor 140 “C. After 2 h, the reaction mixture was cooled and filtered through a pad of Celite which was washed with EtOAc. Solvents were removed. Purification using reverse phase (Giison HPLC, acidic method (ACN water/0.1% TFA), gradient; 61-91%). Giison fractions were neutralized with sat solo. NaHC:::1.8, 8.8 H IH), 7.48 (dd, ./ – 4.3, 8.6 Hz, l H), 730 (d, J:::8.7 Hz, 2H), 6.88 (ddd, J – 2.9, 4.9, 8.7 Hz, 2H), 5.56 (s, 2H), 4.87 (q, 7.0 Hz, 2H), 3.70 (s, 3H), 1.41 (t, J = 3.2 Hz, 3H). ES-MS GammaMu+l f : 443.3.

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; 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

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.

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.

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; JANSSEN PHARMACEUTICA N.V.; WO2008/153752; (2008); A2;,
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

To prepare a-5, a-4 (2.1 g, 0.015 mol) was added to chlorosulfonic acid (4.1 ml, 0.060 mol) at room temperature (RT). Said reaction mixture was stirred overnight under an inert atmosphere such as nitrogen at 60C. The mixture was then poured in ice/water. The precipitate was filtered and dried with toluene in a Buchi-apparatus (2.1 g, yield 60%).

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; TIBOTEC PHARMACEUTICALS LTD; WO2003/97616; (2003); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A common heterocyclic compound, 239097-74-6,Benzo[d]isoxazol-5-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. 239097-74-6

Synthesis of N-benzofdlisoxazol-5-yl-4-propyl-benzenesulfonamide, STX 919 (KRB01047) :; To a solution of 4n-propylbenzenesulphonyl chloride (171 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 (170 mg, 72%), single spot at Rf 0.68 (1: 1 hexane: ethyl acetate). mp 130.0- 130. 6C, HPLC purity 99+% (tR 2.44 min in 10% water-acetonitrile).’H NMR (CDCI3) : No. 8.62 (1H, d, J=1.0 Hz), 7.60 (2H, d, J=8.4 Hz), 7.48 (2H, m), 7.19 (3H, m), 6.86 (1H, s, N-H), 2.58 (2H, t, J=7.5 Hz), 1.58 (2H, sextet, J=7.4 Hz), 0.88 (3H, t, J=7.4 Hz). LCMS: 315.14 (M-). FAB-MS (MH+, deHOsS) : calcd 317.0960, found 317.0962

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-5-amine,239097-74-6,its application will become more common.

Reference£º
Patent; STERIX LIMITED; WO2005/42513; (2005); A1;,
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

Benzisoxazole-3-amine 2 (2.68 g, 20 mmol) was dissolved in water (25 ml) and concentrated HCl (12.5 ml) under vigorous stirring in an ice/water bath. A freshly prepared, ice-cold solution of NaNO2 (1.4 g, 20 mmol) in water (10 ml) was added drop wise to the reaction mixture by keeping the internal temperature between 0 to 5 C. After the completion of addition, the reaction mixture was stirred for an additional 10 min. A freshly prepared solution of sodium azide (1.3 g, 20 mmol) in water (10 ml) was added drop wise to the reaction mixture via an additional funnel while keeping the internal temperature of the reaction mixture below 5 C. Upon complete addition of the sodium azide solution, the reaction mixture was stirred for an additional 20-30 min at 0 C, followed by stirring at room temperature for another 3 h. The reaction mixture was extracted with ethyl acetate EtOAc (25 ml) three times. The combined organic layer was washed with water (25 ml) and brine (25 ml), dried over anhydrous sodium sulphate and concentrated under reduced pressure to get crude benzisoxazole-3-azide 3, which was purified by column chromatography over silica gel (60-120 mesh) using hexane/EtOAc (8:2) as eluent. The pure benzisoxazole-3-azide 3 was stored at 2-5 C in the refrigerator.

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
Article; Ashwini, Nanjundaswamy; Garg, Manoj; Mohan, Chakrabhavi Dhananjaya; Fuchs, Julian E.; Rangappa, Shobith; Anusha, Sebastian; Swaroop, Toreshettahally Ramesh; Rakesh, Kodagahalli S.; Kanojia, Deepika; Madan, Vikas; Bender, Andreas; Koeffler, H. Phillip; Basappa; Rangappa, Kanchugarakoppal S.; Bioorganic and Medicinal Chemistry; vol. 23; 18; (2015); p. 6157 – 6165;,
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

A, in a reaction vessel equipped with a stirrer, a reflux condenser, 5-chloro-3-phenyl-benzisoxazole 0.26 mol, the mass fraction of 30% 2-bromo-5-fluoronitrobenzene solution 390ml, nickel chloride powder 0.46 mol, control the stirring speed at 190 rpm, raise the solution temperature to 78 C, reflux reaction 120 min; B, adding 90% of 4-chlorophenethylamine solution with a mass fraction of 21% slowly add the ethylene glycol dimethyl ether solution with a mass fraction of 37% adding time to control at 110min, continue to reflux reaction 5h. C, add the mass fraction of 27% sodium bicarbonate solution 200ml, reduce the solution temperature to 16 C, molecular sieve bleaching, filtration, the filtrate was concentrated, again lowering the solution temperature to 5 C, the mass fraction of 70% triethylamine solution washing, calcium oxide dehydrating agent dehydration, to give crystals of 2-amino-5-chlorobenzophenone 55.59 g, yield 92%.

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

Reference£º
Patent; Chengdu Qiesite Technology Co., Ltd.; Peng Fei; (9 pag.)CN106083621; (2016); 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

To a solution of intermediate 3 (0.0025 mol) in isopropylether (5 ml) THF (1 ml) was added and the reaction mixture stirred at RT. Phenylisocyanaat (0.0050 mol) was added and the reaction mixture stirred overnight at RT. The precipitate was filtered off, washed with isopropylether and evaporated dried. The residue was further purified over reversed phase HPLC on a Xterra MS C18 column (3′. 5 Rm, 4.6 x 100 mm) with a flow rate of 1.6 ml/min (Elution conditions: three mobile phases (mobile phase A 95% e t..

25mM ammoniumacetate + 5% acetonitrile; mobile phase B: acetonitrile ; mobile phase C: methanol) were employed to run a gradient condition from 100 % A to 50% B and 50% C in 6.5 min., to 100 % B in 1 min, 100% B for 1 min. and re-equilibrate with 100 % A for 1.5 min.) yielding 0.010 g of compound 4 (yield of 5%, Melting Point 246C)., 36216-80-5

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; JANSSEN PHARMACEUTICA N.V.; WO2005/89753; (2005); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics