Structure of 869725-57-5
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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. : | 869725-57-5 |
Formula : | C10H9F3O |
M.W : | 202.17 |
SMILES Code : | OC1CCC2=C1C=CC(C(F)(F)F)=C2 |
MDL No. : | MFCD09839598 |
InChI Key : | FLQUVMBVTFSJRY-UHFFFAOYSA-N |
Pubchem ID : | 24820473 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H320-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-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 |
---|---|---|
92% | Step F 5-(Trifluoromethyl)indan-1-ol To a solution of <strong>[150969-56-5]5-(trifluoromethyl)indan-1-one</strong> (0.7 g, 3 mmol) in THF (5 mL) cooled in an ice bath was added sodium borohydride (0.1 g, 3 mmol) followed by MeOH (1 mL). After being stirred for 30 min, the reaction was quenched with aqueous NaHCO3. The resulting solution was extracted with EtOAc twice. The extracts were washed with brine, dried (MgSO4), filtered and, concentrated. The crude material was purified by flash chromatography on silica eluding with 20% EtOAc/hexane to afford the desired product (0.65 g, 92%) as an oil. LC/MS calculated for C10H9F3O: (M+H)+ 203; found 185.1 (M+H-H2O)+. | |
With sodium tetrahydroborate; ethanol; at 0 - 20℃; for 2.0h; | General procedure: To a solution of Compound IB (5.4 g, 1 mmol) in EtOH (40 mL) was added NaBH4 (0.95 g, 25 mmol) at 0 C. The mixture was stirred room temperature for 2 hours, quenched with 1 N HC1 solution (40 mL), and extracted with dichloromethane (30 mL x 3). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to give Compound 1C: LC-MS (ESI) m/z: 201 [M-OH]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With toluene-4-sulfonic acid; In toluene; for 3.0h;Heating / reflux; Dean-Stark trap; | Step A 6-(Trifluoromethyl)-1H-indene A mixture of <strong>[869725-57-5]5-(trifluoromethyl)indan-1-ol</strong> (1.6 g, 7.9 mmol) and p-toluenesulfonic acid (0.02 g, 0.1 mmol) in toluene (20 mL) was refluxed through a Dean-Stark trap for about 3 h. The solution was concentrated in vacuo and the residue was purified by flash chromatography on silica eluding with 5% EtOAc/hexane to afford the desired product as an oil (1.4 g, 96%). |