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CAS No. : | 1321518-05-1 | MDL No. : | MFCD11878172 |
Formula : | C13H21BN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 248.13 | Pubchem ID : | 45786011 |
Synonyms : |
|
TPSA :Topological Polar Surface Area | - | H-Bond Acceptor Count : | - |
XLogP3 : | - | H-Bond Donor Count : | - |
SP3 : | - | Rotatable Bond Count : | - |
Signal Word: | Warning | Class | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In N,N-dimethyl-formamide; toluene; at 100.0℃;Inert atmosphere; | : in a nitrogen-protected 50 mL single-necked flask, ethyl 1-bromo-5-chloro-6-methylimidazo[1,5-a]pyridine-7-carboxylate (504 mg, 1.59 mmol), <strong>[1321518-05-1]N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)pyridin-2-amine</strong> (396 mg, 1.59 mmol), Pd(dppf)Cl2 (58 mg, 0.08 mmol), Cs2CO3 (1.04 g, 3.19 mmol) were added into 6 mL of toluene:DMF=3:1. The flask was exchanged for three times with nitrogen and the mixture was stirred in an oil bath at 100 C. overnight. The mixture was extracted with ethyl acetate (100 mL) and washed with water (50 mL*2) and saturated brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to provide a crude product. After purified by column chromatography (petroleum ether:EtOAc=5:1), white solids (217 mg, yield: 38%) were obtained. MS (ESI) m/z 359 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; at 20.0℃; for 4.0h; | Commercially available N,N-dimethyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin- 2-amine (0.25 g, 1 mmol) was dissolved in dichloromethane (5 ml_). To the resultant stirring solution was added dropwise at room temperature methyl trifluoromethanesulfonate (0.124 mL, 1.1 mmol). The solution was stirred at room temperature for 4 hours. The reaction mixture was concentrated to remove dichloromethane and the residue was dried in vacuo to obtain a yellow glass/foam, which was directly used for the next step. | |
In dichloromethane; at 20.0℃; for 4.0h; | Commercially available N,N-dimethyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin- 2 -amine (0.25 g, 1 mmol) was dissolved in dichloromethane (5 ml_). To the resultant stirring solution was added dropwise at room temperature methyl trifluoromethanesulfonate (0.124 mL, 1.1 mmol). The solution was stirred at room temperature for 4 hours. The reaction mixture was concentrated to remove dichloromethane and the residue was dried in vacuo to obtain a yellow glass/foam, which was directly used for the next step. | |
In dichloromethane; at 20.0℃; for 4.0h; | Commercially available N,N-dimethyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin- 2-amine (0.25 g, 1 mmol) was dissolved in dichloromethane (5 mL). To the resultant stirring solution was added dropwise at room temperature methyl trifluoromethanesulfonate (0.124 mL, 1.1 mmol). The solution was stirred at room temperature for 4 hours. The reaction mixture was concentrated to remove dichloromethane and the residue was dried in vacuo to obtain a yellow glass/foam, which was directly used for the next step. |
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