Tetrabutylammonium Fluoride → HCID 86699439, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][C:6]([Si](C)(C)C)=[C:5]2[CH2:16][CH2:17][NH:18][C:19](=[O:34])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[CH:21]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:16][CH2:17][NH:18][C:19](=[O:34])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[CH:21]=1Participants
3
Procedure
A mixture of N-(2-(5,7-dichloro-2-(trimethylsilyl)-1H-indol-3-yl)ethyl)-3-(3-fluorobenzyl)benzamide (0.045 g; 0.088 mmol) and tetrabutyl ammonium fluoride (0.263 mL, 1N in THF) was stirred at room temperature for 18 hours and concentrated under reduced pressure. The residue was partitioned between water and dichloromethane. The organic layer was dried and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 2 to 10% ethyl acetate in dichloromethane) to afford 0.018 g (47%) of the title compound as a white solid.