(Diethylamino)sulfur trifluoride → HCID 178505389, compound

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Reaction Steps

In a 10-ml round-bottomed flask under an argon atmosphere, dissolve 85 mg of 4-(3H-imidazo[4,5-c]pyridin-2-yl)-fluoren-9-ol, obtained in Example 3, in 3 ml of dichloromethane. Cool the solution obtained to −60° C. then add, dropwise using a syringe, 41 μL of diethylamino sulphur trifluoride (DAST). Leave to return to room temperature and stir for 45 minutes, then pour the reaction mixture into an aqueous solution with 10% of sodium hydrogen carbonate and extract twice with dichloromethane. Combine the organic phases, dry over sodium sulphate and concentrate under reduced pressure. After purification by chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and methanol (95-5 by volume), we obtain 44 mg of 2-[9(R,S)-fluoro-9H-fluoren-4-yl]-1H-imidazo[4,5-c]pyridine, in the form of a white powder with the following characteristics:

Provenance & Evidence