Structure of 849062-11-9
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 849062-11-9 |
Formula : | C14H11BClF3O3 |
M.W : | 330.50 |
SMILES Code : | FC(C1=CC=C(Cl)C(OCC2=CC=CC=C2B(O)O)=C1)(F)F |
MDL No. : | MFCD07369758 |
InChI Key : | DNZSKCIEUYUZRA-UHFFFAOYSA-N |
Pubchem ID : | 16217921 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H413 |
Precautionary Statements: | P273-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 |
---|---|---|
62% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride; In tetrahydrofuran; water; at 120℃; under 12929.0 Torr;Microwave irradiation; Inert atmosphere; | General procedure: In a CEM Discover vial, each of the intermediate 21-23 (1 equiv.), the appropriate boronic acid a-l (1.5 equiv.), Pd(dppf)Cl2 (0.05 equiv.) and CsF (4 equiv.) were placed. Water (500 μL) and THF (500 μL) were added under N2 atmosphere. The mixture was irradiated for 20-30 min, setting the power at 200 W, the temperature at 120 C, the pressure at 250 psi and the Power Max ON. At completion of the reaction, the vial was cooled to 50 C by gas jet cooling before it was opened. After diluting with 10 mL of aqueous solution of HCl 1 N, the aqueous layer was extracted with ethyl acetate (3 × 10 mL). The organics were then dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by flash chromatography (10% diethyl ether/n-hexane to 40% diethyl ether/n-hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride; In tetrahydrofuran; water; at 120℃; under 12929.0 Torr;Microwave irradiation; Inert atmosphere; | General procedure: In a CEM Discover vial, each of the intermediate 21-23 (1 equiv.), the appropriate boronic acid a-l (1.5 equiv.), Pd(dppf)Cl2 (0.05 equiv.) and CsF (4 equiv.) were placed. Water (500 μL) and THF (500 μL) were added under N2 atmosphere. The mixture was irradiated for 20-30 min, setting the power at 200 W, the temperature at 120 C, the pressure at 250 psi and the Power Max ON. At completion of the reaction, the vial was cooled to 50 C by gas jet cooling before it was opened. After diluting with 10 mL of aqueous solution of HCl 1 N, the aqueous layer was extracted with ethyl acetate (3 × 10 mL). The organics were then dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by flash chromatography (10% diethyl ether/n-hexane to 40% diethyl ether/n-hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride; In tetrahydrofuran; water; at 120℃; under 12929.0 Torr;Microwave irradiation; Inert atmosphere; | General procedure: In a CEM Discover vial, each of the intermediate 21-23 (1 equiv.), the appropriate boronic acid a-l (1.5 equiv.), Pd(dppf)Cl2 (0.05 equiv.) and CsF (4 equiv.) were placed. Water (500 μL) and THF (500 μL) were added under N2 atmosphere. The mixture was irradiated for 20-30 min, setting the power at 200 W, the temperature at 120 C, the pressure at 250 psi and the Power Max ON. At completion of the reaction, the vial was cooled to 50 C by gas jet cooling before it was opened. After diluting with 10 mL of aqueous solution of HCl 1 N, the aqueous layer was extracted with ethyl acetate (3 × 10 mL). The organics were then dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by flash chromatography (10% diethyl ether/n-hexane to 40% diethyl ether/n-hexane). |
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