Structure of 87087-35-2
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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. : | 87087-35-2 |
Formula : | C11H9F3O2 |
M.W : | 230.18 |
SMILES Code : | O=C(OC)/C=C/C1=CC=CC(C(F)(F)F)=C1 |
MDL No. : | MFCD08704704 |
InChI Key : | ZQAIZQSBGPNEEN-AATRIKPKSA-N |
Pubchem ID : | 5314585 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* 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 |
---|---|---|
98% | With bifunctional palladated rasta resin; In N,N-dimethyl-formamide; at 100℃; for 20h;Green chemistry; | General procedure: Catalyst 2c (prepared according Ref. 26b, 133 mg, 6.2 equiv of Pd) was added to a solution of aryl iodide (0.20 mmol, 1.0 m equiv), alkene (0.40 mmol, 2.0 equiv) in DMF (2 mL). The reaction mixture was heated at 100 C for 20 h. After cooling to rt, compound 2c was filtered off under vacuum using a 0.2 μm membrane. The mixture of solvents was concentrated under vacuum to afford pure 3a-j after drying under vacuum (0.1 mbar). The catalyst 2c was then regenerated by reaction with NBu3 (0.16 mL, 0.66 mmol, 3.3 equiv) in DMF at rt for 3 h. Compound 2c was then filtered under vacuum, washed with Et2O (2 mL), and dried under vacuum. |
95% | With triethylamine; In N,N-dimethyl-formamide; toluene; at 100℃; for 20h; | General procedure: Catalyst 1 (prepared according Ref.15a, 7.1 mg,0.05 mequiv of Pd) was added to a solution of aryl iodide (4 mmol,1.0 equiv), methyl acrylate (0.72 mL, 8 mmol, 2.0 equiv), Et3N (0.67 mL,4.8 mmol, 1.2 equiv) in a mixture of toluene (6.7 mL), DMF (3.3 mL) and H2O(0.1 mL). The reaction mixture was heated at 100 C for 20 h. After coolingto rt, 1 was filtered off under vacuum. The mixture of solvents wasconcentrated under vacuum and the residue was purified by flashchromatographyon silica gel to afford pure alkenes after drying under,vacuum (0.1 mbar). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(91-1) Synthesis of 3-(3-trifluoromethylphenyl)-2-propene-1-ol (compound 91-1) 3-(3-Trifluoromethylphenyl)acrylic acid (3.0 g) was dissolved in methanol (30 ml), concentrated sulfuric acid (0.5 ml) was added, and the mixture was stirred at 100C for 5.5 hr. The reaction mixture was concentrated, and the residue was washed with water. The obtained white powder was dissolved in tetrahydrofuran (40 ml), 1M diisobutylaluminum hydride/toluene solution (26 ml) was added dropwise at -78C, and the mixture was stirred as it was at -78C for 2 hr. Saturated Rochelle salt water, water and ethyl acetate were added to the reaction mixture, and the mixture was stirred at room temperature, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give the object product (2.0 g) as a colorless oil. 1H-NMR(DMSO-d6) δ (ppm): 4.15 (2H, td, J=4.9, 0.9Hz), 4.96(1H, t, J=5.5Hz), 6.57(1H, dt, J=16.0, 4.6Hz), 6.67(1H, d, J=15.9Hz), 7.55-7.67(2H, m), 7.75(2H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; at 100℃; for 5.5h; | (91-1) Synthesis of 3-(3-trifluoromethylphenyl)-2-propene-1-ol (compound 91-1) 3-(3-Trifluoromethylphenyl)acrylic acid (3.0 g) was dissolved in methanol (30 ml), concentrated sulfuric acid (0.5 ml) was added, and the mixture was stirred at 100C for 5.5 hr. The reaction mixture was concentrated, and the residue was washed with water. The obtained white powder was dissolved in tetrahydrofuran (40 ml), 1M diisobutylaluminum hydride/toluene solution (26 ml) was added dropwise at -78C, and the mixture was stirred as it was at -78C for 2 hr. Saturated Rochelle salt water, water and ethyl acetate were added to the reaction mixture, and the mixture was stirred at room temperature, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give the object product (2.0 g) as a colorless oil. 1H-NMR(DMSO-d6) δ (ppm): 4.15 (2H, td, J=4.9, 0.9Hz), 4.96(1H, t, J=5.5Hz), 6.57(1H, dt, J=16.0, 4.6Hz), 6.67(1H, d, J=15.9Hz), 7.55-7.67(2H, m), 7.75(2H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | at 200℃; for 16h; | General procedure: A mixture of appropriate substituted methyl cinnamates (6.2 mmol) and 1,2,4-triazol-3-amine (12.4 mmol, 1.04 g) was stirred for 16 h at 200 C. After cooling down, a yellow solid was obtained, which was isolated and purified by silica gel column chromatography with dichloromethane and methanol (50:1) to give a white solid (1a-1o). |
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