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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. : | 100379-00-8 |
| Formula : | C8H11BO2 |
| M.W : | 149.98 |
| SMILES Code : | CC1=C(B(O)O)C(C)=CC=C1 |
| MDL No. : | MFCD01009693 |
| InChI Key : | ZXDTWWZIHJEZOG-UHFFFAOYSA-N |
| Pubchem ID : | 583322 |
| GHS Pictogram: |
|
| 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 |
|---|---|---|
| 97% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 20h; | 3-Bromobenzaldehyde (18.5 g, 100 mmol) and 2,6-dimethylphenylboronic acid (21.0 g, 140 mmol) were dissolved in a mixture of 1 M aqueous sodium carbonate solution (200 mL), ethanol (100 mL) and toluene (200 mL). The air was substituted with argon gas, and tetrakis(triphenylphosphine)palladium(0) (5.78 g, 5.00 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 80C for 20 hr. After cooling the reaction mixture, water was added and the mixture was diluted with ethyl acetate. The insoluble material was filtered off through celite. The organic layer in the filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-10% ethyl acetate/hexane) to give the title compound (20.4 g, yield 97%) as a colorless oil. MS m/z 211 (MH+). |
| 96% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 80℃;Inert atmosphere; | 3-Bromobenzaldehyde (1.8 g, 10 mmol) and (2,6-dimethylphenyl)boronic acid (2.1 g, 14 mmol) were dissolved in a mixture of 1 M aqueous sodium carbonate solution (20 mL), EtOH (10 mL), and toluene (20 mL). After argon substitution, tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. The reaction mixture was stirred under argon atmosphere at 80 C for 20 h. The reaction mixture was cooled, and water was added to the reaction mixture. The mixture was diluted with AcOEt, and the insoluble material was filtered through Celite. The organic layer of the filtrate was washed with brine, dried over anhydrous magnesium sulfate, and concentrated. The crude residue was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 1, v/v) as eluent to afford the product 7a (2.1 g, 96%) as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ: 10.06 (s, 1H), 7.86-7.90 (m, 1H), 7.67-7.69 (m, 1H), 7.61 (t, J = 7.6 Hz, 1H), 7.42-7.46 (m, 1H), 7.11-7.23 (m, 3H), 2.02 (s, 6H). |
| 83% | With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In ethanol; toluene; at 80℃; for 22h;Inert atmosphere; | 3-bromo-benzaldehyde (370.4 mg, 2.002 mmol), 2,6- dimethyl phenyl boronic acid (420.5 mg, 2.804 mmol), saturated aqueous sodium hydrogen carbonate solution (1M solution, 4 mL, 4.001 mmol) ethanol (2.2 mL) of and in a mixed solution of toluene (4 mL), tetrakis (triphenylphosphine) palladium (0) (114.9 mg, 0.099 mmol) was added, under an argon atmosphere and stirred for 22 hours at 80 C.. The reaction mixture was cooled, water (5 mL) and ethyl acetate (10 mL) was added and filtered over Celite (registered trademark). Was separated into aqueous and organic layers, the aqueous layer was extracted twice with ethyl acetate (20 mL), the combined organic layers were extracted with brine (30 mL), further sedge aqueous layer of ethyl acetate (20 and extracted with mL). The combined organic layers were dried over sodium sulfate, the solvent was evaporated, and the residue was purified by column chromatography to give the title compound (hexane: diethyl ether = 60:: 1 ~ 50 1) (347.8 mg, 1.655 mmol, 83 %, to give a colorless oil). |
| 83% | With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In ethanol; water; toluene; at 80℃; for 22h;Inert atmosphere; | 3-bromobenzaldehyde (370.4 mg, 2.002 mmol), 2,6- dimethyl phenyl boronic acid (420.5 mg, 2.804 mmol), saturated aqueous sodium hydrogen carbonate solution (1M solution, 4 mL, 4.001 mmol) ethanol (2.2 mL) of and in a mixed solution of toluene (4 mL), tetrakis (triphenylphosphine) palladium (0) (114.9 mg, 0.099 mmol) was added, under an argon atmosphere and stirred for 22 hours at 80 C.. The reaction mixture was cooled, water (5 mL) and ethyl acetate (10 mL) was added and filtered over Celite (registered trademark). Was separated into aqueous and organic layers, the aqueous layer was extracted twice with ethyl acetate (20 mL), the combined organic layers were extracted with brine (30 mL), further sedge aqueous layer of ethyl acetate (20 and extracted with mL). The combined organic layers were dried over sodium sulfate, the solvent was evaporated, and the residue was purified by column chromatography (hexane: diethyl ether = 60: 1 to 50: 1) toRi purified title compound (347.8 mg, 1.655 mmol, 83%, colorless oil) was obtained. |
| With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 100℃; for 16h; | To a degassed solution of 3-bromobenzaldehyde (500 mg, 2.70 mmol) , (2, 6-dimethylphenyl) boronic acid (608 mg, 4.05 mmol) , and Pd (PPh3) 4 (156 mg, 0.14 mmol) in dioxane (5 mL) was added K2CO3 (2N, 4.05 mL, 8.11 mmol) . The reaction was heated to 100. After 16 h, the mixture was poured into NH4Cl (sat, 25 mL) and extracted with EtOAc (2 x 25 mL) . The combined organic layers were dried over MgSO4 and concentrated. The resulting residue was purified by HPLC (ISCO 40 gram silica gel cartridge, 0 to 40EtOAc/Hex) to give the title compound. |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 85% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; In tetrahydrofuran; for 16.0h;Inert atmosphere; Reflux; | General procedure: A typical procedure is given for the reaction represented by Entry 8 in Table 1. Ligand 2e (6 mg, 0.01 mmol), Pd2(dba)3 (5 mg, 0.005 mmol), 2-methylnaphthyl-1-boronic acid (223 mg, 1.2 mmol), Cs2CO3 (975 mg, 3 mmol) were introduced to a flask under N2 gas. 1-bromo-2-methylnaphthalene (221 mg, 1 mmol) was added into the flask, followed by addition of THF (5 ml) by a syringe. The mixture was stirred under reflux for 24 h, under ambient pressure of N2. The solvent was then removed under reduced pressure. The resultant residual mixture was diluted with H2O (10 ml) and Et2O (10 ml), followed by extraction twice with Et2O. The organic extract was collected and stripped of solvent under vacuum. The product was isolated by column chromatography on silica eluting with hexane/ethyl acetate to give 276 mg (98%) of 2,2'-dimethyl-1-1'-binaphthalene as a solid, which was verified by GC/MS. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In water; acetonitrile; for 6.5h;Inert atmosphere; Microwave irradiation; | Subsequently, 0.96 g of <strong>[38696-20-7]5-bromo-2-phenylpyrimidine</strong> obtained in the above step 1, 1.21 g of 2,6-dimethylphenylboronic acid, 0.87 g of sodium carbonate, 0.76 g of bis (triphenylphosphine) palladium (II) dichloride (Abbreviation: Pd (PPh 3) 2 Cl 2), 15 mL of water and 15 mL of acetonitrile were placed in a recovery flask equipped with a reflux tube and argon bubbling was carried out for 15 minutes. The reaction vessel was heated by irradiating microwave (2.45 GHz 100 W) for 3 hours. Here, 1.21 g of 2,6-dimethylphenylboronic acid, 0.87 g of sodium carbonate and 0.035 g of Pd (PP 3) 2 Cl 2 were placed in a flask and argon bubbling was carried out for 15 minutes. This reaction vessel was heated again by irradiating microwave (2.45 GHz 100 W) for 3 hours. Thereafter, the obtained mixture was suction filtered with water. The obtained solid was purified by flash column chromatography using toluene as a developing solvent to obtain the desired pyrimidine derivative Hppm 2-dmp (white powder, yield 64percent). |
Tags: 2,6-Dimethylphenylboronic acid | Benzene Compounds | Organoboron | Boronic Acids | Aryls | Organometallic Reagents | Boronic Acids/Esters | Organic Building Blocks | 100379-00-8
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| P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
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