Isopropyl iodide → 7-iodo-2-isopropyl-2H-pyrazolo[4,3-b]pyridine

Participants

Reaction Steps

7-Iodo-2H-pyrazolo[4,3-b]pyridine (100 mg, 0.408 mmol), 2-iodopropane (0.049 ml, 0.490 mmol) and sodium hydride (19.59 mg, 0.816 mmol) were combined in DMF (5 mL). The mixture was stirred at room temperature for 1 hour then quenched by the addition of ice. The reaction mixture was purified by preparative HPLC eluting with a gradient of 20-90% 10 mmol NH4HCO3 in 20/80 (v/v) water/acetonitrile in 10 mmol NH4HCO3 in water using a Phenomenex Gemini Prep 5 μm C18, 75×30 mm column to give 7-iodo-2-isopropyl-2H-pyrazolo[4,3-b]pyridine (35 mg, 29.9% yield) and 7-iodo-1-isopropyl-1H-pyrazolo[4,3-b]pyridine (25 mg, 0.34% yield). MS [M+H] found 288.1.

Provenance & Evidence