Boron tribromide → HCID 58415420, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:22][CH2:23][C:24]([N:26]3[CH:30]([CH3:31])[CH2:29][CH2:28][CH:27]3[CH3:32])=[O:25])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17]C)[C:10]3=[N:19][CH:20]=[CH:21][N:9]23)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:22][CH2:23][C:24]([N:26]3[CH:30]([CH3:31])[CH2:29][CH2:28][CH:27]3[CH3:32])=[O:25])[C:16]3[C:15]([OH:17])=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]3=[N:19][CH:20]=[CH:21][N:9]23)=[CH:4][CH:3]=1Participants
4
Procedure
To a solution of 5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-6-methoxy-5H-imidazo[2,1-a]isoindole (190 mg) in CH2Cl2 (2 mL) was added BBr3 (1.7 ml) slowly at 0° C. After 90 min the mixture was quenched with saturated aqueous NaHCO3. The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×). The combined organic layers were dried (Na2SO4), filtered, and concentrated to an off-white solid (179 mg) which was sufficiently pure for use in the next step.