Structure of 1267217-46-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 1267217-46-8 |
Formula : | C8H4F3NO |
M.W : | 187.12 |
SMILES Code : | FC(F)(F)C1=CC2=C(OC=N2)C=C1 |
MDL No. : | MFCD19374815 |
InChI Key : | IYKOEMQMBVZOSI-UHFFFAOYSA-N |
Pubchem ID : | 21749513 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With hydridotetakis(triphenylphosphine)rhodium(I); 1,2-bis-(diphenylphosphino)ethane; In chlorobenzene; for 6h;Inert atmosphere; Reflux; | 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%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | 2-nitro-4- (trifluoromethyl) phenol (500 mg, 2.41 mmol) palladium on carbon (200 mg) was added at 0 under an argon atmosphere in ethanol (10 ml) solution of. After hydrogen substitution, and stirred at room temperature overnight. After completion of the reaction, it was filtered through Celite, and the filtrate was concentrated under reduced pressure. to residue Triethyl orthoformate (2.4 ml, 14.5 mmol) in solution Para tosylic acid monohydrate (23 mg, 0.12 mmol) was added dropwise. Under an argon atmosphere, was stirred 3 h at reflux condition was solidified after completion of the reaction concentrated to dryness. The residue was purified by silica gel column chromatography (hexane / ethyl acetate),To give the title compound (182 mg, 40%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | To a solution of <strong>[1267217-46-8]5-(trifluoromethyl)benzo[d]oxazole</strong> (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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | at 130℃; | A solution of 2-amino-4-(trifluoromethyl)phenol (5g, 28.2mmol) in triethoxymethane (30g, 283mmo1) was heated at 130 C for 5h. The TLC showed reaction to be complete. The solvent was removed under reduced pressure. The residue was purified by column chromatography using silica gel (1 00-200 mesh), eluting with 4% EtOAc in hexane to afford 5-(trifluoromethyl)benzo[d]oxazole as a yellow solid. Yield: 2.5g (48%); 1H NMR (400 MHz, DMSO-d6): 8.20 (5, 1H), 8.10 (5, 1H), 7.63- 7.74 (m, 2H). |
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