Sodium Hydroxide → Imidazo[1,2-A]pyridine-7-carbaldehyde

Participants

Reaction Steps

To imidazo[1,2-a]pyridin-7-yl-methanol (100 mg, 0.7 mmol) suspended in chloroform (5 ml) at room temperature was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane, 0.373 g, 0.9 mmol, 1.3 equiv). This mixture was stirred at room temperature overnight and then dilute sodium hydroxide solution was added and the mixture was stirred for 60 minutes. The mixture was then extracted with dichloromethane and the organic liquors were concentrated in vacuo to furnish imidazo[1,2-a]pyridine-7-carbaldehyde (90 mg) as a white solid. 1H NMR (400 MHz, DMSO-d6): 10.00 (1H, s), 8.67 (1H, d), 8.33 (1H, s), 8.20 (1H, s), 7.86 (1H, d), 7.25 (1H, dd).

Provenance & Evidence