Trifluoroacetic acid → 1H-Indole, 5-fluoro-3-(4-pyridinylmethyl)-

Participants

Reaction Steps

A suspension of (5-fluoro-1H-indol-3-yl)-pyridin-4-yl-methanol (3.36 g, 13.9 mmol) in methylene chloride is treated with triethylsilane (2.48 ml, 15.5 mmol) followed by trifluoroacetic acid (11.9 ml, 155 mmol) at room temperature, stirred overnight and concentrated in vacuo. The resultant residue is treated with saturated Na2CO3 to pH>9 and extracted with methylene chloride. The combined extracts are washed sequentially with water and brine, dried over Na2SO4 and concentrated in vacuo. This residue is purified by flash chromatography (silica gel, CH2Cl2/MeOH: 95/5) to give the title product as a white solid, 2.5 g (80%) mp 141-142° C. (lit. mp 149° C., Malleron et al, J. Med. Chem. 1993, 36, 1194).

Provenance & Evidence