Hydrochloric Acid → HCID 68328046, compound

Participants

Reaction Steps

To a solution of 3-iodo-1H-pyrrolo[3,2-b]pyridine-5-carboxylic acid (0.549 g, 1.906 mmol) in DMF (9.5 mL) at 0° C. was added NaH (60% in mineral oil, 0.191 g, 4.76 mmol). After 30 min at 0° C., p-toluenesulfonyl chloride (0.436 g, 2.287 mmol) was added and the reaction was warmed to RT. After 1 h at RT, the mixture was poured into H2O and the mixture was acidified with 5 M HCl (aq.). The precipitate was collected by filtration, washed with H2O and dried in a vacuum oven overnight to afford 3-iodo-1-((4-methylphenyl)sulfonyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylic acid. (0.663 g, 1.499 mmol, 79%) as a tan solid. MS (ESI, pos. ion) m/z: 442.9 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.35 (3H, br s), 7.44 (2H, d, J=8.22 Hz), 7.96-8.01 (2H, m), 8.10 (1H, d, J=8.80 Hz), 8.47 (1H, d, J=8.80 Hz), 8.54 (1H, s).

Provenance & Evidence