Category: 19932-85-5

19932-85-5, 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. 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

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.

The chemical industry reduces the impact on the environment during synthesis,19932-85-5,6-Bromobenzo[d]oxazol-2(3H)-one,I believe this compound will play a more active role in future production and life.

Reference：
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

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

2-Oxo-2,3-dihydro-benzooxazole-6-carbaldehyde A solution of 6-bromo-3H-benzooxazol-2-one (0.9236 g, 4.31 micromoles) in anhydrous tetrahydrofuran (25 mL) and dimethylformamide (3 mL) under nitrogen was cooled to -78 C. before addition of n-butyllithium (2.5M in hexane) (3.8 mL, 2.2 equiv). After stirring for 10 min at -78 C., 24 mL of sec-butyllithium (1.4 M in cyclohexane, 8 equiv) was added. The reaction was stirred while slowly warming to -40 C. When this temperature was reached, the reaction was quenched by addition of methanol. The reaction mixture was concentrated in vacuo and water was added. The aqueous layer was acidified with 1N HCl (ca. pH 5) and extracted with ethyl acetate (3*50 mL), dried over sodium sulfate, filtered and concentrated to give the product, 0.6402 g (91%). MS (ESI) 164 (MH)+. 1H NMR (400 MHz, DMSO-d6) delta 9.90 (1H, s), 7.79 (1H, d, J=8.0 Hz), 7.74 (1H, s), 7.28 (1H, d, J=8.0 Hz).

19932-85-5, 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.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Reference：
Patent; Chaturvedula, Prasad V.; Chen, Ling; Civiello, Rita; Conway, Charles Mark; Degnan, Andrew P.; Dubowchik, Gene M.; Han, Xiaojun; J. Jiang, Xiang Jun; Karageorge, George N.; Luo, Guanglin; Macor, John E.; Poindexter, Graham; Tora, George; Vig, Shikha; US2004/204397; (2004); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

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

To a solution of 6-bromo-1,3-benzoxazol-2(3H)-one (250 mg, 1.17 mmol) in anhydrous DMF (2 mL) at 0 C was added NaH (60% dispersion in mineral oil, 51.4 mg, 1.29 mmol) under nitrogen. The reaction mixture was stirred for 20 min. Then the reaction mixture was treated with (2-(chloromethoxy)ethyl)trimethylsilane (0.269 mL, 1.52 mmol) drop wise at 0 C and the resulting mixture was stirred for 1 h. The reaction mixture was warmed to 23 C, diluted with water (5 mL) and extracted with EtOAc. The combined organics were dried (Na2SO4), filtered, concentrated under reduced pressure. Purification (FCC, SiO2, 0 to 30% EtOAc/Hexane) afforded the title compound (383 mg, 95.3%).

19932-85-5, 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.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Reference：
Patent; JANSSEN PHARMACEUTICA NV; SAVALL, Bradley M.; SWANSON, Devin M.; WU, Dongpei; AMERIKS, Michael K.; (320 pag.)WO2016/176457; (2016); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

19932-85-5, 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. 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 121 6-Bromo-3-trityl-3 H-benzooxazol-2-one 6-Bromo-3H-benzooxazol-2-one (0.165 g, 0.77 mmol) was added portionwise into a 0 C. suspension of NaH (44.8 mg, 1 mmol, 55%) in dry DMF (4 ml). After 1 hour stirring at room temperature, a solution of triphenylmethylchloride (0.24 g, 0.85 mmol) in DMF (0.5 ml) was added. The reaction mixture was stirred 1 hour at room temperature then quenched with H2O (15 ml). The aqueous phase was extracted with ethyl acetate, the combined organic phases were washed with H2O and brine, dried over Na2SO4 and concentrated to provide 6-bromo-3-trityl-3H-benzooxazol-2-one (0.27 g, 77%) as a beige solid, MS: Mm/e=457.1 (M+H+).

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 reaction routes of 6-Bromobenzo[d]oxazol-2(3H)-one, 19932-85-5

Reference：
Patent; Alanine, Alexander; Buettelmann, Bernd; Neidhart, Marie-Paule H.; Jaeschke, Georg; Pinard, Emmanuel; Wyler, Rene; US2001/47031; (2001); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

19932-85-5, 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. 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

[0156j Triethylamine (0.72 g, 1.0 mL, 7.1 mmol) was added to a stirring a mixture of 6- bromo-2benzoxazilinone (0.89 g, 4.2 mmol) and trityichioride (1.21 g, 4.4 mmol) in CH2C12 (10 mL) for a period of 10 mm. The reaction was monitored by TLC (silica gel) and concentrated after 1 h. The concentrate was diluted with water and sonicated to form a heterogeneous solution. The resulting off-white solid was suction filtered and dried to provide 1 -trityl-6-bromo-2- benzoxazilinone (2.0 g). LCMS: rt 9.45 mm (A), purity 96 %, MS (mle) 456 (MHj.

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 reaction routes of 6-Bromobenzo[d]oxazol-2(3H)-one, 19932-85-5

Reference£º
Patent; RIGEL PHARMACEUTICALS, INC.; SINGH, Rajinder; BHAMIDIPATI, Somasekhar; DING, Pingyu; PAYAN, Donald; GELMAN, Marina; KINSELLA, Todd; WO2015/157093; (2015); 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.

General procedure: To a stirred solution of tert-butyl 6-nitro-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-1carboxylate (CAS: 438200-95-4) (630 mg, 2.26 mmol), 2-(4-(methylsulfonyl)piperazin-1-ylethanol (CAS: 72388-13-7) (940 mg, 4.52 mmol) and PPh; (11186 mg, 4.52 mmol) in THF (30 mL) under Ar atmosphere at 0 C was added DEAD (984 mg, 5.65 mmol). The reaction mixture was stirred under Ar atmosphere at 50 C overnight. The reaction mixture was diluted with H2,O (50 mL) and extracted with EtOAc (3 X 50 mL). The combined organic extracts were washed with brine (SO mL), dried over anhydrous Na2SOuq,filtered and the filtrate was concentrated. The residue was purified bysilica gel chromatography (PE: EA = 1:1, v/v). The fractions were concentrated. The residue was dissolved in PE/EA(3/1, v/v, 20 mL), stirred at room temperature for 16 h, during which time white precipitate was formed. The mixture was filtered and the filter cake was collected to give intermediate 139 (1.36 g, 59% yield) as a white solid. Intermediates 212, 213, and 214 CHCI salt) were prepared respectively via an analogous reaction protocol as described for the preparation offollowing intermediates in the column ?Method used?

19932-85-5, 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.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

It is a common heterocyclic compound, the benzoxazole compound, 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5 its synthesis 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, 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.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

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

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.

General procedure: IV, e.g. bromo-substituted 3H-1,3-benzoxazol-2-one, (1 eq.) was suspended in a 1:1 toluene/EtOH mixture (10 mL per mmol IV). The boronic acid V (1.5 eq.) was added followed by aq. NaCO3 (2 M, 0.55 mL per mmcl IV, 1.1 eq.). The resulting suspension was degassed undernitrogen for 10 mm, followed by addition of Pd(PPh3)4 (0.1 eq.) and heating under microwave irradiation at 100 C for 30 mm. The reaction mixture was diluted with EtOAc (40 mL per mmcl IV), and water (40 mL per mmcl IV) was added. The two phases were separated and the aqueous layer was extracted with EtOAc (2 x 40 mL per mmcl IV). The combined organic phases were dried over Na2SO4, evaporated on silica, and the compound was purified by column chromatography using the Teledyne ISCO apparatus (cyclohexane:EtOAc).The title compound was obtained according to the General Procedure II, starting from 6-bromobenzoxazolone (500 mg, 2.34 mmol) and (4-fluorophenyl)boronic acid (490 mg, 3.50mmol). White solid (450 mg, 42%). 1H NMR (400 MHz, CDCI,) 6 7.08 (m, 3H), 7.33 (dd, J = 8.1, 1.6 Hz, 1H), 7.39 (d, J = 1.4 Hz, 1H), 7.47 -7.52 (m, 2H), 7.91 (s, 1H). MS (ESI) m/z: 228 [M-H].

19932-85-5, 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.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; UNIVERSITA’ DEGLI STUDI DI PARMA; PIOMELLI, Daniele; PIZZIRANI, Daniela; BACH, Anders; SCARPELLI, Rita; MELZIG, Laurin; MOR, Marco; (72 pag.)WO2015/173169; (2015); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

19932-85-5, 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. 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 6-bromo-3H-1,3-benzoxazol-2-one (2.00 g, 9.35 mmol, Intermediate OY) in THF (50 mL) was added t-BuOK (1.26 g, 11.2 mmol). The reaction mixture was stirred at 0 C. for 0.5 hour. Subsequently, [1-[(4-methoxyphenyl)methyl]-2,6-dioxo-3-piperidyl] trifluoromethanesulfonate (4.81 g, 12.6 mmol, Intermediate IQ) in a solution of THF (30 mL) was added dropwise. The resulting reaction mixture was stirred at 20 C. for 0.5 hour under N2. On completion, the reaction mixture was quenched with saturated NH4Cl (100 mL), and extracted with ethyl acetate (100 mL). The combined organic layer was washed with brine (2¡Á100 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (PE:EA:DCM=5:1:2) to give the title compound (3.75 g, 90% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 7.22-7.20 (d, J=8.0 Hz, 1H), 6.89-6.87 (d, J=8.0 Hz, 1H), 4.90-4.86 (m, 1H), 4.47-4.36 (m, 2H) 3.81 (s, 3H), 2.67-2.64 (m, 1H), 2.59-2.54 (m, 2H), 2.40-2.38 (m, 1H). LC-MS (ESI+) m/z 466.9 & 468.9 (M+Na)+.

The chemical industry reduces the impact on the environment during synthesis,19932-85-5,6-Bromobenzo[d]oxazol-2(3H)-one,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

19932-85-5, 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. 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

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).

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 reaction routes of 6-Bromobenzo[d]oxazol-2(3H)-one, 19932-85-5

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