Introduction of a new synthetic route about 1267217-46-8

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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%).

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

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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 5-(Trifluoromethyl)benzo[d]oxazole, 1267217-46-8

1267217-46-8, 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-(Trifluoromethyl)benzo[d]oxazole, cas is 1267217-46-8,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-(trifluoromethyl)benzo[d]oxazole (2g, 10.98mmol) in dry THF (2OmL) was added LiHMDS (6 mL, 1 M in THF, 32.96mmol) at -10 00 slowly. The reaction mixture was stirred at -10 00 for 30 mm and added NBS (2.8g, 16.48mmol). The reaction mixture was allowed to come to rt and stirred for 16h. The TLC showed reaction to be complete. The reaction mixture was quenched with aq NH4CI solution (5OmL) and extracted with ethyl acetate (3x5OmL). The organic layer was washed with saturated aq NaHCO3 solution (5OmL) followed by brine (5OmL), dried (Na2SO4), filtered and concentrated under reduced pressure to give the residue. The residue was purified by column chromatography using silica gel (100-200 mesh), eluting with 3% EtOAc in hexane to afford 2-bromo-5- (trifluoromethyl)benzo[d]oxazole as a white solid. Yield: 900 mg (32%); 1H NMR (400 MHz, CDCI3): 7.99 (5, 1H), 759-7.69 (m, 2H).

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Reference:
Patent; DISCUVA LTD.; MEO, Dr Paul; KHAN, Dr. Nawaz; (284 pag.)WO2018/37223; (2018); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

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Palladium-catalyzed direct arylation of benzoxazoles with unactivated simple arenes

Using CuBr2 as an additive, the Pd-catalyzed intermolecular C-H-C-H cross-coupling between benzoxazoles and unactivated simple arenes has been developed. This protocol provides a straightforward approach for the biological activity of 2-arylbenzoxazole derivatives.

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Benzoxazole – Wikipedia,
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CuCl-Catalyzed direct C-H alkenylation of benzoxazoles with allyl halides

An efficient and concise CuCl-catalyzed C2-alkenylation reaction of benzoxazoles with allyl halides has been established. The distinctive features of this protocol include the use of an inexpensive copper salt as a catalyst, simple and readily available starting materials, and ligand-free conditions. An important application of this method to the synthesis of 1,3-diene substituted benzoxazoles has also been achieved.

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Benzoxazole – Wikipedia,
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Ytterbium(III) Trifluoromethanesulfonate Catalyzed Ring-Opening C(sp3)?N Bond Formation of Benzoxazoles with Propargylic Alcohols

A novel ytterbium(III) trifluoromethanesulfonate [Yb(OTf)3]-catalyzed ring-opening C(sp3)?N bond formation reaction of benzoxazole with propargylic alcohols was established. This reaction uses readily available starting materials and is operationally simple; it thus represents a practical method for the construction of highly functionalized substituted benzenes bearing aldehyde, propargylamine, and hydroxy groups with high atom economy.

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Benzoxazole – Wikipedia,
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ZNF143 inhibition activity and compd. utilizing the same (by machine translation)

PROBLEM TO BE SOLVED: ZNF143 inhibition effect compd. ZNF143 inhibitor and containing the same and a pharmaceutical composition. SOLUTION: eq. (I) or a salt thereof and a compound containing an active component and a and ZNF143 inhibitor. A-B-C-D (I) [A is H, a methyl group, a naphthyl group, a phenyl group or a nitrogen-containing heterocycle; B comprises, And, the C, or N and O ring containing an amide bond; D is a substituted or unsubstituted phenyl group including a single ring or a ring of N or S; C and D are both, may have a substituent, a condensed heterocyclic ring, etc.] selected drawing: fig. 1 (by machine translation)

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Unexpected TFA-catalyzed tandem reaction of benzo[d]oxazoles with 2-oxo-2-arylacetic acids: Synthesis of 3-aryl-2H-benzo[b][1,4]oxazin-2-ones and cephalandole A

A convenient and efficient method for the TFA-catalyzed synthesis of 3-aryl-2H-benzo[b][1,4]oxazin-2-ones via a tandem reaction of benzo[d]oxazoles with 2-oxo-2-arylacetic acids was reported for the first time. The efficiency of this transformation was demonstrated by compatibility with a wide range of functional groups. The synthetic utility of this method was confirmed by the synthesis of the natural product cephalandole A. Moreover, a plausible mechanism for the formation of 3-aryl-2H-benzo[b][1,4]oxazin-2-ones involving ring-opening and cyclization steps is proposed. The present synthetic route to 3-aryl-2H-benzo[b][1,4]oxazin-2-ones could be readily scaled up to gram quantity without difficulty.

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Benzoxazole – Wikipedia,
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Rhodium-catalyzed phenylthiolation reaction of heteroaromatic compounds using alpha-(phenylthio)isobutyrophenone

In the presence of catalytic amounts of RhH(PPh3)4 and 1,2-bis(diphenylphosphino)ethane (dppe), 1,3-benzothiazoles, 1,3-benzoxazoles, and benzothiophene reacted with alpha-(phenylthio) isobutyrophenone giving 2-phenylthio derivatives. Reactive monocyclic heteroaromatics, 1-methyl-1,2,3,4-tetrazole and 2-cyanothiophene were also converted into the 5-phenylthio derivatives. The use of an appropriate phenylthio transfer reagent is crucial for the efficient catalyzed conversion of heteroaromatic C-H bonds into C-S bonds.

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ANTIBIOTIC COMPOUNDS

The present invention relates to antibiotic compounds of formula (I), to compositions containing these compounds and to methods of treating bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Gram-positive and/or Gram-negative bacteria, and in particular in the treatment of infection with, and diseases caused by, Neisseria gonorrhoeae.

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Benzoxazole – Wikipedia,
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1267217-46-8, The synthetic route of 1267217-46-8 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1267217-46-8,5-(Trifluoromethyl)benzo[d]oxazole,as a common compound, the synthetic route is as follows.

To a solution of 5-(trifluoromethyl)benzo[d]oxazole (2g, 10.98mmol) in dry THF (2OmL) was added LiHMDS (6 mL, 1 M in THF, 32.96mmol) at -10 00 slowly. The reaction mixture was stirred at -10 00 for 30 mm and added NBS (2.8g, 16.48mmol). The reaction mixture was allowed to come to rt and stirred for 16h. The TLC showed reaction to be complete. The reaction mixture was quenched with aq NH4CI solution (5OmL) and extracted with ethyl acetate (3x5OmL). The organic layer was washed with saturated aq NaHCO3 solution (5OmL) followed by brine (5OmL), dried (Na2SO4), filtered and concentrated under reduced pressure to give the residue. The residue was purified by column chromatography using silica gel (100-200 mesh), eluting with 3% EtOAc in hexane to afford 2-bromo-5- (trifluoromethyl)benzo[d]oxazole as a white solid. Yield: 900 mg (32%); 1H NMR (400 MHz, CDCI3): 7.99 (5, 1H), 759-7.69 (m, 2H).

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Reference£º
Patent; DISCUVA LTD.; MEO, Dr Paul; KHAN, Dr. Nawaz; (284 pag.)WO2018/37223; (2018); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem