N-bromobutanimide → HCID 178476586, compound

Reaction equation

[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([CH3:20])[C:14]3=[CH:13][N:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[Br:21]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([Br:21])[N:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

Procedure

To (trans)-4-(8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl acetate (5.49 mmol, 1.5 g) in N,N-dimethylformamide (15 ml) was added N-bromosuccinimide (5.49 mmol, 0.977 g) and the mixture was stirred at room temperature. After one hour saturated aqueous sodium hydrogencarbonate solution was added and extracted with dichloromethane three times. The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo. The crude product was purified using column chromatography (silica gel; dichloromethane/methanol (gradient 0 to 5% methanol)) to give the title compound (1.8 g).