Chlorosuccinimide → 3-Bromo-2-chloro-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine
Reaction equation
[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:14]=3[Cl:23])=[O:12])[CH2:10][C:5]2=[N:4][CH:3]=1.C1C(=O)N([Cl:31])C(=O)C1>CN(C)C=O>[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[C:14]=3[Cl:23])=[O:12])[CH2:10][C:5]2=[N:4][C:3]=1[Cl:31]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Bromo-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (E18) (409 mg, 1 mmol) was dissolved in N,N-dimethylformamide (DMF) (5 mL) and NCS (147 mg, 1.100 mmol) was added. The solution was stirred at RT for 24 h. Solvents were removed in vacuo and the residue was purified by flash chromatography (Isolera, 25 g, 0-100% ethyl acetate/iso-hexane) to afford crude product. This was further purified by MDAP to afford desired product in 215 mg.