Benzyl Bromide → methyl 1-benzyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate

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Reaction Conditions

Reaction Steps

Methyl 2 oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate (50 mg, 240 μmol) was dissolved in DMF (0.5 mL) in a 2 mL microwave vial containing a magnetic stirrer bar. Potassium carbonate (100 mg, 720 μmol) was added to the vial followed by benzyl bromide (62 mg, 360 μmol) and tetrabutylammonium iodide (10 mg, 27 μmol). The vial was capped and was heated to 100° C. by microwave irradiation for 5 minutes. The reaction mixture was diluted with EtOAc (3 mL) and of saturated aqueous sodium bicarbonate (3 mL). The organic layer was removed and the aqueous layer was extracted with 2 mL of EtOAc. The organic layers were combined, dried over anhydrous Na2SO4 filtered and evaporated. This yielded 70 mg of a yellow oil which was used without further purification. LCMS (+ESI) m/z=299.1 [M+H]+.

Provenance & Evidence