[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[N:6]1[CH2:10][C:9]2([CH:15]3[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]3)[CH2:11]2)[O:8][C:7]1=[O:18].[Br:19]N1C(=O)CCC1=O>CN(C)C=O.C(Cl)(Cl)Cl>[Br:19][C:5]1[S:1][C:2]([N:6]2[CH2:10][C:9]3([CH:15]4[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]4)[CH2:11]3)[O:8][C:7]2=[O:18])=[N:3][CH:4]=1A solution containing 3′-(thiazol-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one (2.80 g, 10.55 mmol) and N-bromosuccinimide (3.90 g, 21.86 mmole) in N,N-dimethylformamide (15 mL) were stirred at RT overnight. The mixture was diluted with chloroform, washed with saturated aqueous potassium carbonate and then with brine, dried through magnesium sulfate, and then the solvent was evaporated. The residue was purified by flash chromatography using a gradient of ammoniated methanol in chloroform to give the title compound as a pale solid (1.70 g), m/z 343, 345 (MH+).
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