Benzenesulfonyl chloride → 4-Iodo-1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a stirring suspension of NaH (0.9 g) in anhydrous THF (25 ml) at −5° C. was added 4-iodo-1H-pyrazolo[3,4-b]pyridine (5 g) in anhydrous THF (75 ml) and DMF (25 ml). Triethylamine (3 ml) was added and the reaction was stirred for 30 min at 0° C. Benzenesulfonyl chloride (2.9 ml) in anhydrous THF (25 ml) was added dropwise over 10 min and the reaction was stirred for 1 h at 0° C. then quenched with water. The layers were separated and the aqueous was re-extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulfate, filtered and then evaporated to yield a solid residue that was triturated with methanol to give title compound, 4.1 g.

Provenance & Evidence