4-Toluenesulfonyl chloride → HCID 67088968, compound

Participants

Reaction Steps

NaH (1.8 g, 44.9 mmol, 60% suspension in mineral oil) was added portionwise to a cold (0° C.) solution of 3-bromo-1H-pyrazolo[3,4-b]pyridine (3.7 g, 18.7 mmol) in dry THF (50 mL). After 10 minutes, 4-methylbenzene-1-sulfonyl chloride (5.3 g, 28.0 mmol) was added. The cold bath was removed, and the reaction mixture was left at room temperature overnight. The reaction mixture was placed in an ice bath, diluted with ethyl acetate (200 mL) and carefully quenched with water (20 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (7:3) to give 3-bromo-1-tosyl-1H-pyrazolo[3,4-b]pyridine (4.6 g, 70%) as a solid.

Provenance & Evidence