Tetrabutylammonium Fluoride → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylcyclopropyl)-benzo[d]thiazole
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[CH:21]=[C:20]([C:22]4([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH2:24][CH:23]4[Si](C)(C)C)[CH:19]=[CH:18][C:16]=3[N:17]=2)=[C:9]([F:35])[CH:8]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[O:3]1[CH2:4][CH2:5][CH2:6][O:1][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[CH:21]=[C:20]([C:22]4([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)[CH2:23][CH2:24]4)[CH:19]=[CH:18][C:16]=3[N:17]=2)=[C:9]([F:35])[CH:8]=1Participants
3
Conditions
- Temperature
- 110 °C
Procedure
In a reactor bottle were combined 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-(1-phenyl-2-(trimethylsilyl)cyclopropyl)benzo[d]thiazole (1.305 g, 2.6 mmol) and neat tetrabutylammonium fluoride (25 mL, 25 mmol). The reaction mixture was heated to 110° C. in an oil bath and allowed to stir for 2 h. The mixture was cooled and extracted with EtOAc and water, dried over MgSO4 and concentrate in vacuo. Purification by silica gel chromatography afforded 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylcyclopropyl)-benzo[d]thiazole. MS (ESI) m/z: Calculated: 431.1; Observed: 432.1 (M++1).