Dimethyl Sulfoxide → Methyl {1-[(2R)-2-{[(4-fluorophenyl)sulfonyl](methyl)amino}-4-oxobutyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}acetate

Participants

Reaction Conditions

Reaction Steps

To DMSO (1 L, 1.41E+04 mmol) at room temperature was added pyridine sulfur trioxide (202.08 g, 1270 mmol) and the reaction mixture was stirred for 30 min at room temperature (solution A). In another flask, to a stirred solution of methyl {1-[(2R)-2-{[(4-fluorophenyl)sulfonyl](methyl)amino}-4-hydroxybutyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}acetate (273 g, 589 mmol) and Hunig's base (0.425 L, 2433 mmol) in dichloromethane (4 L) at −10° C. was added solution A dropwise over 30 min. The reaction was stirred at −10° C. for 1 h. then quenched by adding ½ saturated brine (4 L); the aqueous layer was neutralized with solid sodium bicarbonate. The layers were then separated and the organic layer was washed with ½ saturated brine (4 L), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography with ethyl acetate to provide the title compound.

Provenance & Evidence