Benzenesulfonyl chloride → 4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine

Participants

Reaction Conditions

Reaction Steps

To a stirring suspension of NaH (1.3 g) in anhydrous THF (25 ml) at −5° C. was added 4-bromo-1H-pyrrolo[2,3-c]pyridine (prepared for example as described in patent US2005/0090529, 5 g) in anhydrous THF (75 ml) over 10 min. The reaction was stirred at −5° C. for 10 min then benzenesulfonyl chloride (3.6 ml) in anhydrous THF (25 ml) was added over 10 min. The reaction was stirred at 0° C. for 1 h then quenched with water. The layers were separated and the aqueous was re-extracted with ethyl acetate. The organics were combined, washed with brine, dried over magnesium sulfate, filtered and then evaporated to yield a residue that was triturated using methanol (25 ml). The resulting solid was collected by filtration, washed sparingly with methanol then dried in vacuo at 45° C. overnight to give title compound, 7.9 g.

Provenance & Evidence