Acetonitrile → 5-bromo-3-(pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a screw top reaction tube was placed 5-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (1.2 g, 2.52 mmol, prepared according to WO2011/149950), pyridin-3-ylboronic acid (371 mg, 3.02 mmol) and trans-dichlorobis(triphenylphosphine)palladium (II) (177 mg, 0.25 mmol). Degassed acetonitrile (16 mL) and 1 N Na2CO3 (16 mL) was added and the reaction tube was purged with argon, sealed and heated at 60° C. for 2 h. The reaction was cooled, filtered through a Celite pad and concentrated under reduced pressure. The residue was partitioned between EtOAc/water and extracted. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give a solid. Trituration of the solid with hexanes and dichloromethane gave the desired compound. LCMS-ESI+: calc'd for C19H14BrN3O2S: 428.0 (M+H+); found: 428.2 (M+H+).

Provenance & Evidence