Water → 6-bromo-3-(4-fluorobenzyl)-2H-pyrido[4,3-e][1,3]oxazin-4(3H)-one

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Reaction Conditions

Reaction Steps

Chloroiodomethane (800 mg, 4.6 mmol) was slowly added to a mixture of 2-bromo-N-(4-fluorobenzyl)-5-hydroxyisonicotinamide (750 mg, 2.3 mmol) and Cs2CO3 (3.0 g, 9.2 mmol) in DMF (20 mL) at 100° C. The mixture was stirred at 100° C. for 2 h. Water was added and the mixture was extracted with EtOAc. After being concentrated, the residue was purified by column chromatography (PE:EtOAc=1:1) to give the product of 6-bromo-3-(4-fluorobenzyl)-2H-pyrido[4,3-e][1,3]oxazin-4(3H)-one (600 mg, yield: 80%). 1H-NMR (Methanol-d4, 400 MHz) δ 8.24 (s, 1H), 7.94 (s, 1H), 7.39 (dd, J=5.6, 8.0 Hz, 2H), 7.09 (t, J=8.8 Hz, 2H), 5.34 (s, 2H), 4.75 (s, 2H). MS (M+H)+: 337/339.

Provenance & Evidence