4-Toluenesulfonyl chloride → 5-fluoro-4-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

To a stirring suspension of sodium hydride (0.595 g, 24.81 mmol) in N,N-dimethylformamide (74.2 ml) was added a solution of 5-fluoro-4-iodo-1H-pyrrolo[2,3-b]pyridine (5 g, 19.08 mmol, Adesis) in N,N-dimethylformamide (10.60 mL). The mixture was stirred under nitrogen for about 30 minutes. para-Toluenesulfonyl chloride (4.00 g, 20.99 mmol) in N,N-dimethylformamide (10.60 ml) was added, and the reaction stirred at room temperature for about an hour. The reaction was quenched by the slow addition of the reaction mixture to a stirring ice-water solution (about 100 mL). The resulting mixture was filtered, and the solid was collected and dried under vacuum overnight to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.28 (s, 1H), 8.09 (d, 1H), 7.98 (d, 2H), 7.43 (d, 2H), 6.67 (d, 1H), 2.35 (s, 3H). MS ESI(+) m/z 416.31 [M+H]+.

Provenance & Evidence