[7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl]methanol → 7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde

Participants

Reaction Steps

[7-(Dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl]methanol (3.0 g, 8.74 mmol) was dissolved in methylene chlorine (175 mL). Manganese dioxide (8.0 g, 92 mmol) was added and the reaction mixture was stirred at room temperature for 20 h. The slurry was filtered through diatomaceous earth to remove the catalyst, and the filtrate was concentrated to a dark oil. Purification by Biotage chromatography (10-30% ethyl acetate in hexanes) provided 7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (1.78 g, 60%) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ4.89 (4H, s), 7.06-7.12 (2H, m), 7.27-7.38 (10H, m), 7.93 (1H, d, J=5.7 Hz), 8.74 (1H, br s), 9.77 (1H, s).

Provenance & Evidence