Trifluoroacetic acid → 3-(5-methyl-4-phenyl-1H-imidazol-2-yl)-3,4-dihydro-1H-isoquinoline
Reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH:24]([C:25]2[NH:26][C:27]([CH3:36])=[C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:29]=2)[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1)=O)(C)(C)C>>[CH3:36][C:27]1[NH:26][C:25]([CH:24]2[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][NH:15]2)=[N:29][C:28]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1Participants
3
Procedure
To a solution of TFA (5 mL) cooled to about 0° C. was added the compound prepared in Step A above (1.10 g, 2.82 mmol), and the reaction mixture stirred for about 30 minutes. The reaction mixture was then removed from the ice bath and allowed to warm to room temperature. Excess TFA was removed under a stream of N2. The residue was partitioned between saturated NaHCO3 and dichloromethane. The aqueous phase was washed with a second portion of dichloromethane and the organic phases combined. The combined organic phase was dried over Na2SO4, then filtered to yield the title product as a solution in dichloromethane, which was used without further purification or isolation.
Workup
- custom