HCID 57893533, compound → HCID 57893538, compound

Participants

Reaction Steps

A mixture of [5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl]methanol (Example 48) (9.74 g, 28.4 mmol) and manganese dioxide (24.6 g, 283.6 mmol) in methylene chloride (584 mL) was stirred at room temperature under a nitrogen atmosphere overnight (15 h). The reaction mixture was filtered through diatomaceous earth to remove the manganese dioxide. Concentration of the filtrate provided the crude material as a dark solid. The crude material was purified by trituration with toluene to give 5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (6.36 g, 65%) as an orange solid: 1H NMR (300 MHz, CDCl3) δ4.84 (4H, s), 6.60 (1H, s), 6.95 (1H, s), 7.21-7.33 (10H, m), 8.63 (1H, s), 9.75 (1H, br s), 9.86 (1H, s).

Provenance & Evidence