Category: 19932-85-5

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 6-Bromobenzo[d]oxazol-2(3H)-one, and cas is 19932-85-5, its synthesis route is as follows.,19932-85-5

General procedure: General Procedure III: Synthesis of compounds of Formula II (Scheme 2b) VI, e.g. bromo-substituted 3H-l,3-benzoxazol-2-one, (1 eq.) was suspended in a 1:1 toluene/EtOH mixture (10 mL per mmol VI). The boronic acid VII (1.5 eq.) was added followed by aq. Na2C03 (2 M, 0.55 mL per mmol VI, 1.1 eq.). The resulting suspension was degassed under nitrogen for 10 min, followed by addition of tetrakis(triphenylphosphine) palladium(O) (0.1 eq.) and heating under microwave irradiation at 100 C for 30 min. The reaction mixture was diluted with EtOAc (40 mL per mmol VI), and water (40 mL per mmol VI) was added. The two phases were separated and the aqueous layer was extracted with EtOAc (2 chi 40 mL per mmol VI). The combined organic phases were dried over Na2S04, evaporated on celite, and the compound was purified by column chromatography using the Teledyne ISCO apparatus (cyclohexane:EtOAc).

With the complex challenges of chemical substances, we look forward to future research findings about 19932-85-5,belong benzoxazole compound

Reference£º
Patent; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; PIOMELLI, Daniele; PAGLIUCA, Chiara; PIZZIRANI, Daniela; BACH, Anders; REALINI, Natalia; DE VIVO, Marco; (112 pag.)WO2015/173168; (2015); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5, it is a common heterocyclic compound, the benzoxazole compound, its synthesis route is as follows.,19932-85-5

6-bromo-3H-1,3-benzoxazol-2-one (8A) (1.78g, 13 mmol) was dissolved in tetrahydrofuran (15 ml), and under N2 protection, a solution of 2M isopropyl magnesium chloride in tetrahydrofuran (7 mL, 14 mmol) were added at -10C. The temperature was raised to 0C, followed by reaction for 1 hour. A solution of n-butyllithium in tetrahydrofuran (21 ml, 52 mmol) was added at -25C, followed by reaction at -10C for 30 min. N,N-dimethylformamide (9.5 g, 130 mmol) was added at -10C, and the temperature was gradually raised to room temperature, followed by reaction for 0.5 hours. The reaction solution was poured into water (50 ml) containing 5 g citric acid, and was extracted by addition of ethyl acetate (50 ml). The aqueous phase was extracted with ethyl acetate (50 mL*1). The organic phases were combined. The organic phase was dried over anhydrous sodium sulfate and filtered.The filtrate was concentrated under reduced pressure, made into a slurry with 50% (v/v) ethyl acetate/petroleum ether, and purified by silica gel column chromatography (ethyl acetate/petroleum ether (v/v) = 0:1 to 1:4) to obtain the title compound 2-oxo-3H-1,3-benzoxazole-6-carbaldehyde (8B) as a white solid (1.60 g, yield 75.4%). 1H NMR (400 MHz, DMSO-d6) delta 12.16 (s, 1H), 9.92 (s, 1H), 7.78 (dd, 1H), 7.74 (d, 1H), 7.29 (d, 1H). LCMS m/z=164.1[M+1].

As the rapid development of chemical substances, we look forward to future research findings about 19932-85-5

Reference£º
Patent; Sichuan Haisco Pharmaceutical Co., Ltd.; WEI, Yonggang; QIU, Guanpeng; LEI, Bolin; LU, Yonghua; ZHENG, Suxin; EP3375781; (2018); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19932-85-5,6-Bromobenzo[d]oxazol-2(3H)-one,as a common compound, the synthetic route is as follows.

To a solution of the compound of Preparation A (0.348 g; l . lmmol) and 6-bromobenzo[< Joxazol-2(3H)-one (prepared as described in EP 1988077, 0.214 g; lmmol) in DMF (4.2 mL) was added K2C03 (0.212g, 1.53mmol). The reaction proceeded at 60C for 16h. Water (20 mL) was added and the resulting mixture was extracted three times with EA (3 x 20 mL). The evaporation residue was purified by CC (EA-Hept) to afford the title compound (0.396 g; 88% yield) as an orange solid. 1H NMR (d6-DMSO) delta 7.69 (d, J = 1.8 Hz, 1H); 7.47 (dd, J = 1.8, 8.3 Hz, 1 H); 7.30 (d, J = 8.3 Hz, 1H); 4.00-3.91 (overlapped m, 1H); 3.91-3.81 (overlapped m, 1H); 3.1 1 (s, 3H); 2.66-2.56 (m, 1H); 2.19-2.10 (m, 1H); 1.58 (s, 3H); 1.35 (s, 9H). MS (ESI, m/z): 448.04 [M+H+] for Ci7H22N06BrS; tR = 0.92 min. 19932-85-5, 19932-85-5 6-Bromobenzo[d]oxazol-2(3H)-one 29859, abenzoxazole compound, is more and more widely used in various fields.

Reference£º
Patent; ACTELION PHARMACEUTICALS LTD; CHAPOUX, Gaelle; DIETHELM, Stefan; GAUVIN, Jean-Christophe; PANCHAUD, Philippe; SURIVET, Jean-Philippe; (90 pag.)WO2017/37039; (2017); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 6-Bromobenzo[d]oxazol-2(3H)-one, and cas is 19932-85-5, its synthesis route is as follows.,19932-85-5

Intermediate 13: 2-oxo-2,3-dihydrobenzo[d]oxazole-6-carbonitrile To a solution of 6-bromo benzoxazolinone (2 g, 9.4 mmol) in DMF (20 mL) was added CuCN (16.79 g, 188 mmol), and the reaction was stirred at 175 C. for 6 h. The reaction progress was monitored by TLC (100% EtOAc). The reaction was diluted with EtOAc (10 mL) and filtered through Celite brand filter agent. The organic layer was concentrated and purified by column chromatography (silica gel, 0-50% EtOAc in hexanes) to give the title compound. MS (ESI pos. ion) m/z: 158.9 (MH-).

With the complex challenges of chemical substances, we look forward to future research findings about 19932-85-5,belong benzoxazole compound

Reference£º
Patent; AMGEN INC.; BISWAS, Kaustav; CHEN, Jian J.; GORE, Vijay Keshav; HARRIED, Scott; HORNE, Daniel B.; KALLER, Matthew R.; MA, Vu Van; SHAM, Kelvin; ZHONG, Wenge; US2014/45855; (2014); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO464,mainly used in chemical industry, its synthesis route is as follows.,19932-85-5

General procedure: Heteroarylboronic acid (1.3 equivalents), aryl bromide (1 equivalent), and tetrakis(triphenylphosphine) palladium(0) (5mol %) were suspended in DME to give a 0.07-0.1M solution of boronic acid under nitrogen atmosphere. A 0.5M aqueous solution of sodium carbonate (6 equivalents) was added. The mixture was refluxed for 3.5-14h, cooled to room temperature, diluted with water and extracted several times with ethyl acetate. The combined extracts were dried over anhydrous MgSO4, concentrated and purified by flash chromatography and were if necessary recrystallized.

With the synthetic route has been constantly updated, we look forward to future research findings about 6-Bromobenzo[d]oxazol-2(3H)-one,belong benzoxazole compound

Reference£º
Article; Grombein, Cornelia M.; Hu, Qingzhong; Rau, Sabrina; Zimmer, Christina; Hartmann, Rolf W.; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 788 – 796;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5, it is a common heterocyclic compound, the benzoxazole compound, its synthesis route is as follows.,19932-85-5

General procedure: Toluene (4.5mL) was added to a flask containing 6-bromo-3,4-dihydroquinolin-2(1H)-one (300mg, 1.33mmol), 3-(trifluoromethoxy)aniline (231muL, 1.73mmol), Pd2(dba)3 (15.2mg, 0.02mmol), 2-dicyclohexylphosphino-2?,4?,6?-triisopropylbiphenyl (31.6mg, 0.07mmol) and NaOt-Bu (192mg, 2.00mmol) under an argon atmosphere. The mixture was stirred at 100C for 9h. After cooling, the reaction mixture was diluted with EtOAc, and filtered through a pad of Celite. The filtrate was concentrated in vacuo. Crude material was purified by flash chromatography with n-hexane/EtOAc (2:3) to afford the desired diaryl amine 11i

19932-85-5 is used more and more widely, we look forward to future research findings about 6-Bromobenzo[d]oxazol-2(3H)-one

Reference£º
Article; Takeuchi, Tomoki; Oishi, Shinya; Kaneda, Masato; Misu, Ryosuke; Ohno, Hiroaki; Sawada, Jun-Ichi; Asai, Akira; Nakamura, Shinya; Nakanishi, Isao; Fujii, Nobutaka; Bioorganic and Medicinal Chemistry; vol. 22; 12; (2014); p. 3171 – 3179;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5, it is a common heterocyclic compound, the benzoxazole compound, its synthesis route is as follows.,19932-85-5

To a solution of the compound of Preparation A (0.348 g; l . lmmol) and 6-bromobenzo[< Joxazol-2(3H)-one (prepared as described in EP 1988077, 0.214 g; lmmol) in DMF (4.2 mL) was added K2C03 (0.212g, 1.53mmol). The reaction proceeded at 60C for 16h. Water (20 mL) was added and the resulting mixture was extracted three times with EA (3 x 20 mL). The evaporation residue was purified by CC (EA-Hept) to afford the title compound (0.396 g; 88% yield) as an orange solid. 1H NMR (d6-DMSO) delta 7.69 (d, J = 1.8 Hz, 1H); 7.47 (dd, J = 1.8, 8.3 Hz, 1 H); 7.30 (d, J = 8.3 Hz, 1H); 4.00-3.91 (overlapped m, 1H); 3.91-3.81 (overlapped m, 1H); 3.1 1 (s, 3H); 2.66-2.56 (m, 1H); 2.19-2.10 (m, 1H); 1.58 (s, 3H); 1.35 (s, 9H). MS (ESI, m/z): 448.04 [M+H+] for Ci7H22N06BrS; tR = 0.92 min. As the rapid development of chemical substances, we look forward to future research findings about 19932-85-5 Reference£º
Patent; ACTELION PHARMACEUTICALS LTD; CHAPOUX, Gaelle; DIETHELM, Stefan; GAUVIN, Jean-Christophe; PANCHAUD, Philippe; SURIVET, Jean-Philippe; (90 pag.)WO2017/37039; (2017); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19932-85-5,6-Bromobenzo[d]oxazol-2(3H)-one,as a common compound, the synthetic route is as follows.,19932-85-5

To a solution of 6-bromo-3H-benzoxazol-2-one (15 g; ca. 0.07 mol, containing 8-9% 3H-benzooxazol-2-one) and triethylamine (11.1 mL, 0.08 mol) in DCM (250 mL) was added trityl chloride (21.5 g, 0.08 mol). The solution was stirred at room temperature for 18 h and was then washed with distilled water (3 x 250 mL), brine (250 mL) and dried (MgSO4), filtered and evaporated to give an off-white colored solid. The product was dissolved in refluxing EtOAc then allowed to cool to room temperature with constant stirring for several hours. The solids were collected (21.16 g) and the filtrate was concentrated until precipitation occurred, re-heated (reflux) for several hours and allowed to cool with stirring to encourage a second crystallization (7.88 g).

19932-85-5 6-Bromobenzo[d]oxazol-2(3H)-one 29859, abenzoxazole compound, is more and more widely used in various fields.

Reference£º
Patent; AVENTIS PHARMACEUTICALS INC.; WO2006/86705; (2006); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19932-85-5,6-Bromobenzo[d]oxazol-2(3H)-one,as a common compound, the synthetic route is as follows.

General procedure: The crude product above (2.0mmol) was dissolved in DMF (20mL). The corresponding benzo[d]oxazol-2(3H)-one (2.4mmol) and Cs2CO3 (782mg, 2.4mmol) was added to the solution. The reaction mixture was stirred at 50C for 5h and then cooled to room temperature. The mixture was diluted with water (40mL) and then was extracted with ethyl acetate (20mL¡Á3). The combined organic layer was washed by saturated sodium chloride solution for three times, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford 11. White solid (27%, 4 steps). 1H NMR (300MHz, CDCl3) delta 8.73 (d, J=5.1Hz, 1H), 8.20 (s, 1H), 7.81 (d, J=8.9Hz, 1H), 7.55 (d, J=8.7Hz, 1H), 7.41 (s, 1H), 7.39 (s, 1H), 7.06 (d, J=8.8Hz, 1H), 6.72 (d, J=5.3Hz, 1H), 4.52 (t, J=4.9Hz, 2H), 4.39 (d, J=5.2Hz, 2H). MS (ESI): 463.1 [M+H]+. Purity: >95%, 19932-85-5

As the paragraph descriping shows that 19932-85-5 is playing an increasingly important role.

Reference£º
Article; Lu, Dong; Shen, Aijun; Liu, Yang; Peng, Xia; Xing, Weiqiang; Ai, Jing; Geng, Meiyu; Hu, Youhong; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 191 – 200;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19932-85-5,6-Bromobenzo[d]oxazol-2(3H)-one,as a common compound, the synthetic route is as follows.

To a deoxygenated mixture of tert-butyl ( (5- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2- yl) pyridin-2-yl) methyl) carbamate (62.5 mg, 0.187 mmol) , 6-bromobenzo oxazol-2 (3H) -one (40.0 mg, 0.187 mmol) , cesium carbonate (183 mg, 0.561 mmol) in DMF (0.93 mL) was added PdCl2(dppf) (21 mg, 0.028 mmol) and water (0.033 mL, 1.9 mmol) and the resulting mixture was heated at 140 for 30 min under microwave irradiation. The mixture was cooled and partitioned between EtOAc and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (0-5 MeOH in EtOAc) to afford the Boc protected intermediate. To a solution of this intermediate (18 mg, 0.053 mmol) in DCM (0.18 mL) was bubbled gaseous HCl for 1 min. The mixture was stirred for 1 h and then concentrated to afford the title compound. MS: m/z 242.24 (M + 1), 19932-85-5

19932-85-5 6-Bromobenzo[d]oxazol-2(3H)-one 29859, abenzoxazole compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; COOKE, Andrew J.; PITTS, Daniel; JOHNSON, Adam; BESHORE, Douglas C.; HURZY, Danielle; MITCHELL, Helen; FRALEY, Mark; MCCOMAS, Casey; SCHIRRIPA, Kathy; MERCER, Swati P.; NANDA, Kausik; MENG, Dongfang; WU, Jane; BABAOGLU, Kerim; LI, Chun Sing; MAO, Qinghua; QI, Zhiqi; (156 pag.)WO2016/54807; (2016); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem