Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1) → 3-fluoro-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

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Reaction Steps

To a solution of 2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.063 g, 0.28 mmol) in CH2Cl2 (4 mL) was added 1-fluoropyridinium triflate (0.104 g, 0.42 mmol) and stirred at rt for 3 days. The mixture was partitioned between EtOAc and 0.1N HCl. The organic phase was washed with 0.1N HCl and sat'd brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography (10-50% EtOAc-hexanes gradient) to afford the title compound as a white solid (0.015 g, 22% yield, 94% purity): MS (ES) m/z 243 (M+1).

Provenance & Evidence