1-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate [Fluorinating Reagent] → 4-[2-carbamoyl-3-fluoro-1-(4-fluoro-benzyl)-1H-indol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester

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Reaction Steps

4-[2-Carbamoyl-1-(4-fluoro-benzyl)-1H-indol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.0155 gm, 0.034 mmol) was dissolved in dichloromethane and 1-fluoro-2,4,6-trimethylpyridinium triflate (85%, 0.012 gm, 0.035 mmol) was added and the reaction mixture was stirred at room temperature overnight. The mixture was transferred onto two preparative thin layer chromatography plates and eluted with 1/1 ethyl acetate/hexane, then further purified on two analytical thin layer chromatography plates (1/1 ethyl acetate/hexane), and then additionally purified on two more analytical plates (35/65 ethyl acetate/hexane) to give 4-[2-carbamoyl-3-fluoro-1-(4-fluoro-benzyl)-1H-indol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.009 gm, 56% yield).

Provenance & Evidence