1,10-Phenanthroline → HCID 67089033, compound

Participants

Reaction Steps

3-Iodo-1-(4-methoxybenzyl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (2.0 g, 4.88 mmol), 1,10-phenanthroline (0.879 g, 4.88 mmol), copper (I) iodide (0.929 g, 4.88 mmol), potassium fluoride (4.96 g, 34.1 mmol), and 2-methoxyethanol (11.1 g, 146 mmol) were suspended in toluene (65 mL) and stirred at reflux for 20 hours. The mixture was cooled, diluted with EtOAc, filtered through a plug of silica, and concentrated. The crude product was purified via column chromatography eluting with 6:4 EtOAc-hexanes to afford 1-(4-methoxybenzyl)-3-(2-methoxyethoxy)-5-nitro-1H-pyrazolo[3,4-b]pyridine (400 mg, 1.12 mmol, 22.9%).

Provenance & Evidence