Triethylsilane → 3-(4-Fluorophenyl)-5-methylindoline

Participants

Reaction Steps

To the cooled solution of 3-(4-fluorophenyl)-5-methyl-1H-indole (2 g, 0.0088 mol) in TFA (60 mL) was added triethylsilane (6 mL) dropwise at 0° C., and the reaction mixture was stirred for 4 h at RT. After completion of reaction (monitored by TLC), solvent was removed under reduced pressure, the residue treated with saturated sodium bicarbonate solution, and extracted with EtOAc (3×150 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the product purified by column chromatography (10% EtOAc:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch) to provide the desired compound as a yellow colored oil (1.2 g, 60% yield).

Provenance & Evidence