Benzisoxazole | Page 619 of 644 | Heterocyclic Building Blocks-Benzisoxazole

A new synthetic route of 5-Chloro-3-phenylbenzo[c]isoxazole

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.

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

1) Weigh 180 g of raw material 5-chloro-3-phenyl-2,1-benzisoxazole into 1.5 L of anhydrous methanol and 1.5 L of acetonitrile,After stirring and dissolving, add 10g Pd/C catalyst with Pd content of 3%, stir and mix to form material I,The flow rate of the slurry pump was adjusted so that the flow rate of the material I was 40.0 g/min and entered the preheating module of the microreactor. 2) Adjust the flow rate of the H2 gas flowmeter to 350ml/min, and directly enter the reaction module group and material I to undergo catalytic hydrogenation reaction without preheating.As shown in Figure 2, the molar ratio of 5-chloro-3-phenyl-2,1-benzisoxazole to hydrogen is 1:1.2, the reaction temperature is 80C, the residence time of the reaction is 35s, and the reaction pressure is 1.0Mpa; then enter the cooling module, cooling module temperature is 30 C,Collect the reaction solution from the outlet of the cooling module, recover the catalyst by filtration, and recover the solvent by distillation under reduced pressure.The residue was recrystallized from 80% ethanol solution to obtain the target product 2-amino-5-chlorobenzophenone, 168.96g, yield 92.79%, purity 99.68%.

Reference£º
Patent; Heilongjiang Xinchuang Bio-technology Development Co., Ltd.; Ren Jiqiu; Yang Kun; Li Haitao; (10 pag.)CN107935872; (2018); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A new synthetic route of 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,36216-80-5,Benzo[d]isoxazol-3-amine,its application will become more common.

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

A mixture of benzo[d]isoxazol-3-amine and a sulfonyl chloride in pyridine (0.5 ml.) was stirred at room temperature for 64 hours. The reaction was concentrated and diluted with 5% aqueous HCI (1 ml.) and sonicated for a minimum of 30 minutes. The resulting precipitate was collected by filtration and a portion of the crude material (50 mg or less) was purified by preparative mass-directed HPLC to give the desired product. See Table B for reaction components and amounts used.

Reference£º
Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; MORROW, Benjamin, Joseph; FOITZIK, Richard, Charles; HEMLEY, Catherine, Fae; CAMERINO, Michelle, Ang; BOZIKIS, Ylva, Elisabet, Bergman; WALKER, Scott, Raymond; (321 pag.)WO2019/243491; (2019); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

A new synthetic route of Benzo[d]isoxazol-3-amine

A mixture of benzo[d]isoxazol-3-amine and a sulfonyl chloride in pyridine (1 ml.) was stirred at room temperature for 16 hours when a second portion of benzenesulfonyl chloride was added and stirred for an additional 64 hours. The reaction was concentrated and diluted with 5% aqueous HCI (1 ml.) and sonicated for a minimum of 30 minutes. The resulting precipitate was collected by filtration and purified either by preparative mass-directed HPLC (up to 50 mg of crude material) or by silica gel column chromatography (0-40% EtOAc/petroleum benzine 40-60 C) to give the desired product. See Table C for reaction components and amounts used as well as purification conditions.

A new synthetic route of Benzo[d]isoxazol-5-amine

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.

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-vl-3-chloro-2-methvl- benzenesulfonamide, STX 918 (KRB01046):; To a solution of 3-chloro-2-methylbenzenesulphonyl chloride (176 mg, 0.783 mmol) in dichloromethane (4 mL) was added pyridine (150 iuL, 1.86 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-1, 2-benzisoxazole [27] (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 (178 mg, 74%), single spot at Rf 0.69 (1: 1 hexane: ethyl acetate). mp 111.9-112. 4C, HPLC purity 97% (tR 2.44 min in 10% water-acetonitrile).’H NMR (CDCl3) : No. 8.62 (1H, d, J=1.0 Hz), 7.81 (1H, dd, J=7.9, 1.2 Hz), 7.55 (1H, dd, J=7.9, 1.0 Hz), 7.45 (2H, m), 7.17 (2H, m), 6.77 (1H, s, N-I), 2.72 (3H, s). LCMS: 321.01 (M-). FAB-MS (MH+, C14H11CIN203S) : calcd 323.0257, found 323.0271

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

The origin of a common compound about 719-64-2

The preparation method is as follows: 5-chloro-3-phenyl 2,1-benzisoxazole (commercially available) (0.3 mmol, 68.7 mg), phenylacetaldehyde (0.6 mmol, 72.0 mg), copper powder (0.06) Methanol, 3.8 mg) and silver triflate (0.03 mmol, 8.0 mg) were added to a 25 ml Schlenk tube, and the reaction tube was replaced with oxygen three times under reduced pressure.Hexafluoroisopropanol (2 ml) was added and stirred at 110 C for 30 hours.After completion of the reaction, a column chromatography of silica gel of 100-200 mesh was added, and the solvent was evaporated under reduced pressure. The crude product was subjected to silica gel column chromatography, eluting with petroleum ether and ethyl acetate ( petroleum ether: ethyl acetate = 20:1) The liquid was eluted, and the elution was carried out by TLC elution. The eluate containing the desired product was collected, and the desired product eluent was combined and evaporated to give the quinoline compound of the formula i above, yield 69%. This material is a red solid.

Reference£º
Patent; Jiangnan University; Zou Lianghua; Zhu Hao; Zhu Shuai; Li Pinggui; Yan Cheng; (12 pag.)CN110204486; (2019); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

Some scientific research about Benzo[d]isoxazol-3-amine

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.

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 new synthetic route of Benzo[d]isoxazol-3-amine

Example 148: N-(benzo[d]isoxazol-3-yl)-2,4-dimethoxybenzenesulfonamide 148 A solution of 2,4-dimethoxybenzenesulfonyl chloride (0.18 g, 0.75 mmol) and benzo[d]isoxazol-3-amine (0.10 g, 0.75 mmol) in pyridine (1 ml.) was irradiated in the microwave at 1 10 C for 2 hours. The resultant mixture was loaded onto silica gel and the product purified twice by column chromatography (4 g Si02 cartridge, 0-45% EtOAc in petroleum benzine 40-60 C then 4g Si02 cartridge, 0-35% EtOAc in petroleum benzine 40-60 C) to yield two batches (78 mg and 5 mg) of [183] the title compound (total mass 83 mg, 33 % yield) as white solids. 1H NMR (400 MHz, CDCI3) d 8.1 1 (d, J = 8.05 Hz, 1H), 7.79 (s, 1H), 7.70 (d, J = 8.81Hz, 1H), 7.57 – 7.50 (m, 1H), 7.47 – 7.40 (m, 1H), 7.37 – 7.29 (m, 1H), 6.50 (d, J = 2.27 Hz, 1H), 6.42 (dd, J = 2.25, 8.81Hz, 1H), 3.98 (s, 3H), 3.81 (s, 3H). LCMS-B: rt 3.20 min, m/z = 356.8 [M+Na]+, 334.8 [M+H]+.

New downstream synthetic route of 651780-27-7

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.

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

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).

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

New downstream synthetic route of 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

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

A new synthetic route of 5-Amino-3-methylbenzo[d]isoxazole

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,851768-35-9,5-Amino-3-methylbenzo[d]isoxazole,its application will become more common.

A common heterocyclic compound, 851768-35-9,5-Amino-3-methylbenzo[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. 851768-35-9

Synthesis of N-(3-methyl-benzo[d]isozazol-5-yl)-4-propyl- benzenesulfonamide, STX875 (KRB01028) :; To a solution of 4n-propylbenzenesulphonyl chloride (124 mg, 0.567 mmol) in dichloromethane (3 rnL) was added pyridine (110 pL, 1.35 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-3-methyl-1, 2-benzisoxazole (80 mg, 0.54 mmol) was added. The resulting mixture was stirred for 3 h at room temperature, then saturated NaHCO3 solution (8 mL) was added and the mixture was extracted into ethyl acetate (15 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 pale pink solid (150 mg, 84%), single spot at Rf 0.62 (1: 1 hexane: ethyl acetate). mp 119.5-120. 0C, HPLC purity 99+% (tR 2.29 min in 10% water-acetonitrile). 1H NMR (CDCI3) : No. 7.57 (2H, d, J=8.4 Hz), 7.40 (1H, d, J=2.2 Hz), 7.37 (1H, d, J=8.8 Hz), 7.20 (2H, d, J=8.4 Hz), 7.10 (1H, dd, J=8.8, 2.2 Hz), 6.71 (1H, s, N-/d), 2.59 (2H, t, J=7.5 Hz), 2.51 (3H, s), 1.59 (2H, sextet, J= 7.5 Hz), 0.88 (3H, t, J=7.5 Hz). LCMS: 314.07 (M- CH3). FAB-MS (MH+, Ci7HisN203S) : calcd 331.1116, found 331.1117

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