N-bromobutanimide → 6-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one
Reaction equation
[C:1]1([C:7]2[CH:17]=[N:16][C:10]3[O:11][CH2:12][C:13](=[O:15])[NH:14][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:18]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[Br:18][C:17]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][C:9]2[NH:14][C:13](=[O:15])[CH2:12][O:11][C:10]=2[N:16]=1Participants
Conditions
- Temperature
- 80 °C
Procedure
In a 10 ml microwave vial was 7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (50 mg, 0.221 mmol) and N-bromosuccinimide (78.6 mg, 0.441 mmol) in dimethylformamide (1 ml). The reaction mixture was heated to 80° C. under microwave irradiation for 30 minutes. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (10 ml). The organic solution was washed with water (2×10 ml) and brine (2×10 ml). The organic phase was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified via Biotage chromatography (gradient 0% to 5% methanol in dichloromethane) to give the title compound as a yellow solid (61 mg, 90%). 1H NMR (500 MHz, CD3OD) δ 7.48-7.32 (5H, m), 7.12 (1H, s), 4.82 (2H, s).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- washThe organic solution was washed with water (2×10 ml) and brine (2×10 ml)
- dry with materialThe organic phase was dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude residue was purified via Biotage chromatography (gradient 0% to 5% methanol in dichloromethane)
Sources & evidence
- ORD record
- ord-5dae0fc0f9e44152b2cbd27c281b82db
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221838B2
Reaction notes
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