1H-Pyrrolo(2,3-b)pyridine → 1H-Indazole

Participants

Reaction Steps

To the Rink resin (corresponding to fragment A9 of table I, 11 g, 0.85 mmol/g, 9.35 mmol) in anhydrous DMF (15 ml), 5-nitro-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (2.9 g, 14.03 mmol), TBTU (4.5 g, 14.03 mmol) and DIPEA (3.62 g, 28.05 mmol) were added. The reaction mixture was shaken at room temperature for 20 hours and then the resin was isolated by filtration. The resin was washed sequentially with DMF (25 ml), DCM (25 ml), DMF (25 ml), DCM (25 ml), MeOH (25 ml), DCM (25 ml), MeOH (25 ml), DCM (25 ml), MeOH (25 ml), TBME (25 ml×2) and dried in vacuo to give the resin bound 7-azaindole (12.5 g). 0.01 g of the resin were cleaved (1 ml of 40% TFA/DCM) to give an off-white solid (0.0014 mg, 82%).

Provenance & Evidence