Structure of 1160184-14-4
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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. : | 1160184-14-4 |
Formula : | C5H2Br2IN |
M.W : | 362.79 |
SMILES Code : | IC1=CC(Br)=NC(Br)=C1 |
MDL No. : | MFCD13185521 |
InChI Key : | RPLWQERFYBEHLW-UHFFFAOYSA-N |
Pubchem ID : | 71464233 |
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 |
---|---|---|
74.1% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 70.0℃; for 5.0h; | 9.8 g (27.0 mmol) of <strong>[1160184-14-4]2,6-dibromo-4-iodopyridine</strong>,Phenylboronic acid 3.29 g (27.0 mmol),1.15 g (1 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium) and 8.3 g (60 mmol) of K2CO3 were dissolved in 500 ml of a THF / H2O (9/1 by volume) mixed solution, the mixture was stirred at 70 C at 5 h. The reaction mixture was cooled to room temperature, 300 ml of water was added, and the mixture was extracted three times with 300 ml of ethyl ether. The resulting organic layer was dried over magnesium sulfate, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography to obtain 6.26 g (yield: 74.1%) of intermediate B-2. The resulting compound was identified by LC-MS |
40% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 60.0℃; for 3.0h; | The reaction vessel was charged with phenylboronic acid (2.06 g, 16.9 mmol)<strong>[1160184-14-4]2,6-dibromo-4-iodopyridine</strong> (6.13g, 16.9mmol),Tetrakistriphenylphosphine palladium (0.2 g, 0.17 mmol),Potassium carbonate (10.6 g, 76.6 mmol),Toluene 120mL, ethanol 40mL and distilled water 40mL,Stir at 60 C for 3h.After completion of the reaction, the distilled water was quenched and extracted with ethyl acetate. The organic layer is dried over MgSO4. The solvent was distilled off under reduced pressure and then purified on a silica gel column to give compound 2-20-A (2.12 g, 40%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 12.0h;Reflux; Inert atmosphere; | In a 250 mL round bottom flask,<strong>[1160184-14-4]2,6-dibromo-4-iodopyridine</strong> (10 mmol),3,5-diphenyl-1-boronic acid-benzene (21 mmol) and Pd(PPh3) 4 (0.3 mmol)Add to toluene (30 mL) / ethanol (20 mL) andA mixture of potassium carbonate (12 mmol) in water (10 mL) was refluxed for 12 h under nitrogen atmosphere.The resulting mixture was cooled to room temperature, added to water, and then filtered over EtOAc EtOAc. The intermediate product HB058-1 was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 12.0h;Reflux; Inert atmosphere; | In a 250 mL round bottom flask 2,6-dibromo-4-iodo-pyridine (10 mmol),2,4-diphenyl-6-borate-pyrimidine (12 mmol)And Pd (PPh3) 4 (0.3 mmol) were added to toluene (30 mL) / ethanol (20 mL)And a mixture of potassium carbonate (12 mmol) in water (10 mL),The reaction was refluxed for 12 h under a nitrogen atmosphere.The resulting mixture was cooled to room temperature, added to water, and then filtered through a pad of diatomaceous earth. The filtrate was extracted with dichloromethane, then washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated.The crude product was purified by silica gel column chromatography to obtain the final product HB03-1. |