N-Methyl-2-(trimethylsilyl)-1H-indole-5-acetamide → N-Methyl-1H-indole-5-acetamide

Participants

Reaction Steps

N-Methyl-2-(trimethylsilyl)-1H-indole-5-acetamide (8) (2.5 g, 0.00961 mol) was dissolved in CH3CN (50 mL) and HF (1.9 g of a 50% aqueous solution, 0.048 mol) was added. The mixture was stirred at RT for 1.5 h. The solvent was removed in vacuo and the residue was dissolved in EtOAc. The organic phase was extracted with saturated aqueous NaHCO3 and then with brine, dried over MgSO4, filtered and evaporated in vacuo. Silica gel chromatography (10-100% EtOAc gradient in hexane) of the concentrate afforded the product (0.86 g, 47.6%).

Provenance & Evidence