N-bromobutanimide → 7-bromo-4-ethyl-4-pyridin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one
Reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([C:11]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[N:16]2[C:17](=[O:23])[NH:18][C:19]3=[CH:20][CH:21]=[CH:22][C:14](=[C:15]23)[O:13][CH2:12]1)[CH3:10]>C(#N)C.C(O)(=O)C>[Br:1][C:22]1[C:14]2[O:13][CH2:12][C:11]([CH2:9][CH3:10])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[N:16]3[C:17](=[O:23])[NH:18][C:19]([C:15]=23)=[CH:20][CH:21]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
N-Bromosuccinimide (70 mg, 0.4 mmol) was added to a solution of 4-ethyl-4-pyridin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (80 mg, 0.4 mmol) in acetonitrile (5 mL) and acetic acid (10 mL) cooled to 0° C. The reaction was stirred for 30 min, was concentrated to remove residual acetic acid, and the resulting residue was dissolved in ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, washed with brine, dried over magnesium sulfate, filtered, and concentrated to give crude 7-bromo-4-ethyl-4-pyridin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (0.07 g. 80%). LCMS calculated for C16H15BrN3O2 (M+H)+: m/z=360.1, 362.1. found: 359.8, 361.8.
Workup
- concentrationwas concentrated
- customto remove residual acetic acid
- dissolutionthe resulting residue was dissolved in ethyl acetate
- washThe organic layer was washed with saturated aqueous sodium bicarbonate
- washwashed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-682fad09d32b4b3790741ee20520cf74
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227985B2
Reaction notes
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