Month: June 2021

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.

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, 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; 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

Name is Benzo[d]oxazol-2-amine, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 4570-41-6, its synthesis route is as follows.

Step 4:To a solution of 3-(4-fluorophenyl)-2-(3-methanesulfonylphenyl)propionic acid (200 mg, 0.62 mmol) and 2-aminobenzoxazole (87 mg, 0.65 mmol) in CH2Cl2 (10 mL) was added DMAP (23 mg, 0.19 mmol) and EDC.HCl (144 mg, 0.75 mmol).The reaction mixture was stirred at room temperature overnight and then concentrated in vacuo.Purification by chromatography (silica, 0-50percent ethyl acetate/hexanes stepwise gradient)) afforded N-benzooxazol-2-yl-3-(4-fluorophenyl)-2-(3-methanesulfonyl-phenyl)propionamide (62 mg, 23percent): m.p. 99-100° C., LC/MS-ESI observed [M+H]+ 439.

4570-41-6, 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.,4570-41-6 ,Benzo[d]oxazol-2-amine, other downstream synthetic routes, hurry up and to see

Reference：
Patent; Brotherton-Pleiss, Christine E.; Walker, Keith A. M.; US2012/149718; (2012); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

701-16-6, 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. 5-Fluoro-2-methylbenzo[d]oxazole, cas is 701-16-6,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

5-Fluoro-2-Methyl-6-Nitrobenzoxazole (10) Concentrated sulfuric acid (60 mL) was stirred mechanically and cooled in an ice/water bath. To this was gradually added 5-fluoro-2-methylbenzoxazole (9), (20 g, 0.132 Moles), at such a rate that the temperature stayed at 15-20 C., over a 15-20 minute period. A solution of concentrated sulfuric acid (11 mL), and concentrated nitric acid (10 mL), was prepared and added drop by drop to the benzoxazole solution at such a rate that the temperature was maintained at approximately 10 C.

The chemical industry reduces the impact on the environment during synthesis,701-16-6,5-Fluoro-2-methylbenzo[d]oxazole,I believe this compound will play a more active role in future production and life.

Reference：
Patent; Eastman Kodak Company; US2005/101784; (2005); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 5-Bromobenzo[d]oxazole, and cas is 132244-31-6, its synthesis route is as follows.

198 mg (ie 1 mmol) of 5-bromobenzoxazole, 203 mg (ie 1.5 mmol) of 2-methyl-3-bromopropene, 240 mg (ie 3 mmol) of lithium tert-butoxide and 10 mg 0.1mmol) cuprous chloride, then add 2mL toluene, stirred at 110oC for 2 hours, after the reaction was concentrated to a petroleum ether: ethyl acetate volume ratio of 250: 1 as eluant by silica gel column chromatography to obtain5-bromo-2- (2-methyl-1-propenyl) benzoxazole, which structural formula is as follows:The compound was a light yellow solid in 80% yield with NMR data as follows:

132244-31-6, 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.,132244-31-6 ,5-Bromobenzo[d]oxazole, other downstream synthetic routes, hurry up and to see

Reference：
Patent; Inner Mongolia University; Chen Shufeng; Li Die; (6 pag.)CN107266386; (2017); A;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 5-(Trifluoromethyl)benzo[d]oxazole, and cas is 1267217-46-8, its synthesis route is as follows.

General procedure: In a two-necked flask equipped with a reflux condenser were placed RhH(PPh3)4 (4 mol%, 11.5 mg), 1,2-bis(diphenylphosphino)ethane (8 mol%, 8.0 mg), 1,3-benzothiazole 5 (0.25 mmol, 27.3 mL), and (alpha-phenylthio)isobutyrophenone 6 (0.25 mmol, 64.0 mg) in chlorobenzene (0.25 mL) under an argon atmosphere, and the solution was heated at reflux for 3 h. The mixture was purified by flash column chromatography on silica gel giving 7 (55.8 mg, 92%) and isobutyrophenone 8 (34.3 mg, 93%) with the recovery of 5 (3.5 mg, 10%) and 6 (0.8 mg, 1%).

1267217-46-8, 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.,1267217-46-8 ,5-(Trifluoromethyl)benzo[d]oxazole, other downstream synthetic routes, hurry up and to see

Reference：
Article; Arisawa, Mieko; Toriyama, Fumihiko; Yamaguchi, Masahiko; Tetrahedron Letters; vol. 52; 18; (2011); p. 2344 – 2347;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 2-Chloro-6-fluorobenzo[d]oxazole, and cas is 153403-53-3, its synthesis route is as follows.

Example 2 [Show Image] To N,N-dimethylformamide (10 mL) were added trans-4-amino-1-cyclohexanecarboxylic acid ethyl ester (2.08 g, 10 mmol) and triethylamine (5.0 mL, 36 mmol). The reaction solution was cooled below 5 C and stirred. To the suspension, was added N,N-dimethylformamide (4mL) solution in Compound 3A(2.23 g, 13 mmol)(EP572893) dropwise, the reaction mixture was stirred at room temperature for 2 hours. To the reaction solution, were added ethyl acetate (25 mL) and 5%-citric acid solution (25 mL). The organic layer was extracted, the water layer was repeatedly extracted with ethyl acetate (25 mL). Each of the organic layer was mixed, and the mixed organic layer was washed with 5%-brine and dried over magnesium sulfate anhydrous. The solvent was removed under reduced pressure, and the residue was purified using silica gel chromatography (n-hexane – ethyl acetate 100:0?50:50(v/v)) to yield 3.04g of Compound 3B (yield 98 %) as a colorless solid. 1H-NMR (CDCl3) delta: 1.26 (t, J = 7.10 Hz, 3H), 1.27-1.38 (m, 2H), 1.58-1.68 (m, 2H), 2.04-2.13 (m, 2H), 2.23-2.34 (m, 2H), 3.63-3.79 (m, 1H), 4.14 (q, J = 7.10 Hz, 2H), 5.31 (s, 1H), 6.86-6.93 (m, 1H), 7.00 (dd, J = 8.24, 2.53 Hz, 1H), 7.23 (dd, J = 8.24, 4.82 Hz, 1H). MS: [M + H]+ m/z 307.1

153403-53-3, 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.,153403-53-3 ,2-Chloro-6-fluorobenzo[d]oxazole, other downstream synthetic routes, hurry up and to see

Reference：
Patent; Shionogi & Co., Ltd.; EP2505584; (2012); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Name is 2-Methylbenzo[d]oxazol-6-amine, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 5676-60-8, its synthesis route is as follows.

INTERMEDIATE B2 7V-(4-Bromo-2-hydroxyphenyl)acetamide – -To a cooled (0 0C) suspension of 2-methyl-l,3-benzoxazol-6-amine (Intermediate Bl; 1.96 g, 13.2 mmol) in 1 M HBr (40 niL) was carefully added NaNO2 (1.38 g, 20 mmol). After stirring for 10 min, a solution of CuBr (2.92 g, 20 mmol) in water (14 mL) was added and the mixture was stirred at 0 0C for 5 min. The ice-bath was removed and the mixture was stirred overnight and then 25% aqueous ammonia (5 mL) was added. The mixture was extracted with EtOAc (500 mL) and the organic layer was concentrated. The residue was purified by flash chromatography on silica using MeOH/CHCl3 (0.05:1) as eluent. Yield 1.47 g (32%). Analytical HPLC: purity 100% (System A); LRESIMS (ESI+) m/z = 230/232 (M+H)+.

5676-60-8, 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.,5676-60-8 ,2-Methylbenzo[d]oxazol-6-amine, other downstream synthetic routes, hurry up and to see

Reference：
Patent; INOVACIA AB; WO2009/150144; (2009); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 2-Benzoxazolinone, and cas is 59-49-4, its synthesis route is as follows.

To a mixture of 3H-benzooxazol-2-one (20 g, 0.15 mol) in DCM (500 mL) was added bromine (8.34 mL, 0.16 mol). After stirring at room temperature for 19.5 h, the orange precipitate that had formed was filtered off and washed with DCM until the orange color was washed out. The filtrate was concentrated to approximately 33% of its original volume and filtered and washed as before. The combined solids weighed 28.36 g. 1H NMR indicated the product was clean albeit contained ca. 8-9% starting material meaning the true yield of product was 26.72 g, 84%.

59-49-4, 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.,59-49-4 ,2-Benzoxazolinone, other downstream synthetic routes, hurry up and to see

Reference：
Patent; AVENTIS PHARMACEUTICALS INC.; US2008/138413; (2008); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is Benzo[d]oxazol-2-amine, and cas is 4570-41-6, its synthesis route is as follows.

20 mg of (S)-1-(3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolopyrrolidin-1-yl)prop-2-en-1-one obtained in Step 3 was dissolved in 520 mL of DMF, and 13 mg of benzo[d]oxazol-2-amine, 3.65 mg of PdCl2(PPh3)2 and 23 muL of DBU were added thereto. The mixture was stirred for 2 hours at 120 degrees in a carbon monoxide atmosphere, and then the solvent was removed using an evaporator. DMSO was added to the residue, and the mixture was purified by reverse phase preparative HPLC purification (water/acetonitrile (0.1percent formic acid)), and thus 1.9 mg of the title compound was obtained as a white solid.

4570-41-6, 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.,4570-41-6 ,Benzo[d]oxazol-2-amine, other downstream synthetic routes, hurry up and to see

Reference：
Patent; Taiho Pharmaceutical Co., Ltd.; IGUCHI, Satoru; HOSOI, Fumihito; SAGARA, Takeshi; EP2947086; (2015); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

59-49-4, 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. 2-Benzoxazolinone, cas is 59-49-4,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Step 1: N-Bromosuccinimide (26.6 g, 0.15 mol) was added to a stirred solution of 2-benzoxazolinone (20.0 g, 0.15 mol) in glacial acetic acid (220 mL), and the mixture was stirred at room temperature for 3 days. The reaction mixture was poured into H2O (1.2 L), and the white solid that formed was collected. Recrystallization from hot EtOH (300 mL) gave bromide 1 (22.1 g, 70%) as an off-white solid: mp 190-195 C.; IR (KBr): 3278, 1779, 1736, 1623 cm?1; 1H NMR (300 MHz, CD3OD): ?7.41 (d, J=2 Hz, 1H), 7.32 (dd, J=5, 2 Hz, 1H), 6.99 (d, J=5 Hz, 1H); CI MS (methane) (m/z): 215 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis,59-49-4,2-Benzoxazolinone,I believe this compound will play a more active role in future production and life.

Reference：
Patent; Nikam, Sham Shridhar; Scott, Ian Leslie; Sherer, Brian Alan; Wise, Lawrence David; US2003/236252; (2003); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem