C(N(CC)CC)C.[C:8]([C:11]1[CH:12]=[C:13]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:14]2[O:19][CH2:18][CH2:17][N:16]([CH2:20][C:21]#[N:22])[C:15]=2[CH:23]=1)(=[O:10])[CH3:9].[Br:28]N1C(=O)CCC1=O.C(OCC)(=O)C>O1CCCC1>[Br:28][CH2:9][C:8]([C:11]1[CH:12]=[C:13]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:14]2[O:19][CH2:18][CH2:17][N:16]([CH2:20][C:21]#[N:22])[C:15]=2[CH:23]=1)=[O:10]
Triethylamine (0.76 ml, 5.5 mmol) and tert-butyl dimethylsilyltrifluoromethanesulfonate (0.73 g, 5.5 mmol) were added to a solution of [6-acetyl-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-4-yl]methyl cyanide (0.5 g, 1.8 mmol) in tetrahydrofuran (50 ml) while cooling on ice and the mixture was stirred at the same temperature for 30 minutes, after which N-bromosuccinimide (0.49 g, 2.7 mmol) was added and stirring was continued for 30 minutes. Ethyl acetate was added, the reaction mixture was washed with brine and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and then the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (310 mg) as a light yellow solid.
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