N-Bromosuccinamide → HCID 117728336, compound
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][C:13]1[N:14]=[C:15]2[C:20]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[N:19][CH:18]=[CH:17][N:16]2[CH:27]=1.[Br:28]NC(=O)CCC(N)=O>C(Cl)Cl>[Br:28][C:17]1[N:16]2[CH:27]=[C:13]([CH2:12][O:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)[N:14]=[C:15]2[C:20]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[N:19][CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of compound 31a (5.0 g, 14 mmol) and N-bromosuccinamide (2.5 g, 14 mmol) in DCM (300 mL) at 0° C. was allowed to stir at rt for 10 min. The reaction mixture was diluted with DCM (600 mL) and washed with saturated NaHCO3 (500 mL) and brine (500 mL). The DCM layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue obtained was triturated with EtOAc to give compound 31b as a white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C20H18BrN5O2: 440.1 (M+H). found: 440.0.