Tetrabutylammonium Fluoride → Methyl 6-chloro-1H-indole-5-carboxylate
Reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8](C#C[Si](C)(C)C)[C:7]([NH:16][C:17](=O)[CH3:18])=[CH:6][C:5]=1[Cl:20].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:20][C:5]1[CH:6]=[C:7]2[C:8]([CH:18]=[CH:17][NH:16]2)=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:21]Participants
4
Procedure
A solution of methyl-2-chloro-4-acetamido-5-(2-trimethylsilylethynyl)-benzoate (1.9 g, 5.9 mmol) in THF (15.0 mL) containing tetrabutyl ammonium fluoride (1.9 g, 6.0 mmol) was heated to reflux for 6 h under nitrogen. The reaction mixture was concentrated to dryness and the residue partitioned between ethyl acetate (25 mL) and water (25 mL). The organic layer was washed with water, dried (MgSO4) and concentrated to dryness. The residue was purified by silica gel flash chromatography using 25% ethyl acetate in heptane to afford the title compound as a light brown powder (0.98 g, 86%), m/z 210 (M+H).