Structure of 219834-96-5
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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. : | 219834-96-5 |
Formula : | C17H15BO3 |
M.W : | 278.11 |
SMILES Code : | OB(C1=C2C=CC=CC2=CC=C1OCC3=CC=CC=C3)O |
MDL No. : | MFCD16295233 |
InChI Key : | COGFIOKWQKNPLW-UHFFFAOYSA-N |
Pubchem ID : | 22715022 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-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 |
---|---|---|
With bis(benzonitrile)palladium(II) dichloride; cesium fluoride; (R)-4-phenyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine; In tetrahydrofuran; at 70℃; for 4h;Inert atmosphere; Schlenk technique; | General procedure: A Schlenk tube was charged with 0.25 mmol of naphthyl halide, 0.0025 mmol of Pd precursor, 0.00375 mmol of the appropriate chiral ligand, 0.5 mmol of boronic acid, and 1.25 mmol of base. Anhydrous solvent was added, the flask was sealed and the mixture was stirred and heated at the corresponding temperature. The reaction mixture was treated with 10 mL of distilled water, extracted with 3 x10 mL of CH2Cl2, dried over MgSO4, and purified by flash chromatography to obtain the corresponding products. The conversion and selectivity was monitored by gas chromatography. The ee values were determined by High Performance Liquid Chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis(benzonitrile)palladium(II) dichloride; cesium fluoride; (R)-4-phenyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine; In tetrahydrofuran; at 70℃; for 4h;Inert atmosphere; Schlenk technique; | General procedure: A Schlenk tube was charged with 0.25 mmol of naphthyl halide, 0.0025 mmol of Pd precursor, 0.00375 mmol of the appropriate chiral ligand, 0.5 mmol of boronic acid, and 1.25 mmol of base. Anhydrous solvent was added, the flask was sealed and the mixture was stirred and heated at the corresponding temperature. The reaction mixture was treated with 10 mL of distilled water, extracted with 3 x10 mL of CH2Cl2, dried over MgSO4, and purified by flash chromatography to obtain the corresponding products. The conversion and selectivity was monitored by gas chromatography. The ee values were determined by High Performance Liquid Chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With hydrogenchloride; water; at 20℃; for 0.75h; | To a suspension of aryl bromide (6.26 g, 20.0 mmol) in Et2O (75 mL) at -78 C was added n-BuLi (8.0 mL, 2.5 M, 20 mmol) in hexanes, and the mixture was stirred at 0 C for 1 h. After recooling to -78 C, the mixture was treated with trimethyl borate (2.5 mL, 22 mmol) and allowed to warm to room temperature overnight. The resulting mixture was quenched with 1 M HCl (50 mL) and stirred at room temperature for 45 min. The phases were separated, and the extraction was completed with CH2Cl2. The combined organic extracts were dried (MgSO4) and evaporated in vacuum to give the desired compound as a white powder (4.62 g, 83%), which was used in the next step without further purification. For analytical purposes, a small amount of the product was recrystallized from MeOH/H2O: mp 133.0-135.0 C. 1H NMR (400.14 MHz, d4-MeOH) 5.20 (s, 2H), 7.28-7.60 (m, 9H), and 7.56-7.88 (m, 2H). 13C{1H} NMR (63 MHz, d4-MeOH) 71.95, 115.4, 124.8, 127.7 (2C), 128.4, 128.9, 129.5, 129.6, 130.7 (2C), 131.8, 137.2, 139.0, and 159.7. |
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