Perfluoro-1-butanesulfonyl fluoride → HCID 59596643, compound

Participants

Reaction Steps

To a stirred solution of 3-hydroxy-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (695 mg, 3.16 mmol) and DMAP (19 mg, 0.16 mmol) in DCM (10 ml) at 0° C. was added DIPEA (1.35 ml, 7.58 mmol) and nonafluorobutylsulfonyl fluoride (0.74 ml, 4.10 mmol). After 10 minutes the reaction was warmed to room temperature and stirred for an additional 4.5 hours. The reaction mixture was diluted with DCM (50 ml) and washed with water (30 ml). The organic phase was isolated, dried over sodium sulphate then filtered and evaporated to give a yellow oil. The oil was purified by flash chromatography (Si-PPC, pentane:ethyl acetate, gradient 100:0 to 60:40) to afford the title compound as a colourless oil which crystallised on standing (1.43 g, 90%). LCMS (method B): RT=3.28 min, M+H+=505.

Provenance & Evidence