Water → 1-Tosyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde (16.7 g, 114 mmol) in DMF (150 mL) was added to a chilled (0° C.) mixture of dry DMF (300 mL) and sodium hydride (4.88 g, 122 mmol, 60% dispersion in mineral oil). This was stirred at 0° C. for 30 minutes, and a DMF solution (100 mL) of tosyl chloride (21.8 g, 114 mmol) was then added slowly over a ten minute period. The mixture was then allowed to warm to room temperature and stirred for 3 hours. Water (500 mL) was then added, and the solids were collected to give 1-tosyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (29.7 g, 87%). 1H NMR (400 MHz, d6-DMSO) δ 10.07 (s, 1H), 8.43-8.49 (m, 2H), 8.08-8.13 (m, 2H), 7.44-7.50 (m, 3H), 2.37 (s, 3H).

Provenance & Evidence