o-Toluenesulfonyl chloride → HCID 49758932, compound

Participants

Reaction Steps

To a solution of 4-bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine (D) (1.89 g, 8.16 mmol) in DMF (15 mL) at 0° C. was added NaH (60% in oil, 328 mg) followed by toluenesulfonylchloride (1.72 g, 8.98 mmol). The reaction mixture was warmed to RT and additional NaH (60% in oil, 2×200 mg) was added at 1 h intervals. After a further 1 h, EtOAc was added and the reaction was quenched with sat'd NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layer was washed with water, brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (SiO2, 7% EtOAc in hexanes) provided 4-bromo-5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine (E) (1.81 g, 58%) as an off white solid. LC/MS Tret=4.8 min, (M+H+) 386.6.

Provenance & Evidence