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CAS No. : | 14733-73-4 | MDL No. : | MFCD01664246 |
Formula : | C7H4BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DMHTZWJRUUOALC-UHFFFAOYSA-N |
M.W : | 214.02 | Pubchem ID : | 26853 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
37% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In N,N-dimethyl-formamide; at 110℃; for 1h;Microwave irradiation; Inert atmosphere; Sealed tube; | Under an atmosphere of nitrogen, a mixture of (4-(((tert- butoxycarbonyl)amino)methyl)phenyl)boronic acid (commercially available from for example Aldrich) (387 mg, 1.54 mmol), 5-bromobenzo[d]oxazol-2(3H)-one (commercially available from for example Aldrich) (300 mg, 1.40 mmol) and sodium carbonate (446 mg, 4.21 mmol) in DMF (4 mL) was treated with dicholoro[l,l'- bis(diphenylphosphino)ferrocene]palladium(II) (commercially available from for example Aldrich) (72 mg, 0.098 mmol) then sealed and heated in a Biotage "Initiator" microwave at 110 C for 1 hr. The cooled product mixture was treated with dichloromethane (50 mL) and water (10 mL). The mixture was separated and the organic fraction was evaporated to dryness. The product was subjected to purification by mass-directed automated preparative HPLC (formic acid modifier) to afford the title compound (178 mg, 0.52 mmol, 37 % yield). LCMS RT= 1.03 min, ES+ve m/z 341 [M+H]+. |
37% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In dichloromethane; water; N,N-dimethyl-formamide; at 110℃; for 1h;Inert atmosphere; Microwave irradiation; | Under an atmosphere of nitrogen, a mixture of <strong>[489446-42-6](4-(((tert-butoxycarbonyl)amino)methyl)phenyl)boronic acid</strong> (commercially available from for example Aldrich) (387 mg, 1.54 mmol), 5-bromobenzo[d]oxazol-2(3H)-one (commercially available from for example Aldrich) (300 mg, 1.40 mmol) and sodium carbonate (446 mg, 4.21 mmol) in DMF (4 mL) was treated with dicholoro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) (commercially available from for example Aldrich) (72 mg, 0.098 mmol) then sealed and heated in a Biotage "Initiator" microwave at 110 C. for 1 hr. The cooled product mixture was treated with dichloromethane (50 mL) and water (10 mL). The mixture was separated and the organic fraction was evaporated to dryness. The product was subjected to purification by mass-directed automated preparative HPLC (formic acid modifier) to afford the title compound (178 mg, 0.52 mmol, 37% yield). LCMS RT=1.03 min, ES+ve m/z 341 [M+H]+. |
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