Citric Acid → 1-[(2,4-Difluorophenyl)methyl]pyrrolo[2,3-c]pyridine-5-carbohydroxamic acid

Participants

Reaction Conditions

Reaction Steps

1-(2,4-Difluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid. To ethyl 1-(2,4-difluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (0.30 g, 1.58 mmol) in methanol (3 mL) was added sodium hydroxide (0.076 g, 3.16 mmol) in water (0.5 mL). The reaction was heated in a SmithCreator® (microwave reactor from Personal Chemistry) to 100° C. for five minutes. The reaction solution was poured into water (30 mL) and the pH was adjusted to 2-3 by addition of citric acid. The precipitate that formed was collected by filtration and dried in vacuo to provide the title compound as a white powder (0.15 g, 55% yield). 1H NMR (DMSO-d6): δ; 8.97 (s, 1H), 8.35 (s, 1H), 7.82 (d, 1H, J=3.2 Hz), 7.28–7.38 (m, 2H), 7.09 (t, 1H, J=8.4 Hz), 6.76 (d, 1H, J=3.2 Hz), 5.67 (s, 2H). LCMS (API-ES, M+H+): 289.1.

Provenance & Evidence