Dimethylformamide → HCID 66759972, compound

Participants

Reaction Steps

To a cooled (0° C.) suspension of sodium hydride (15 mg, 0.37 mmol) in DMF (200 μL) was added dropwise a solution of 2-chloro-4-iodo-furo[2,3-c]pyridin-7-ylamine (100 mg, 0.340 mmol) in DMF (1 mL). After 5 min, methyl iodide (23 μL, 0.37 mmol) was added and the reaction stirred at room temperature for 2 h. The reaction was then quenched with water (30 mL). The quenched mixture was extracted with dichloromethane (2×10 mL). The combined organic fractions were washed with water (1×10 mL) and brine (1×10 mL), dried over sodium sulfate, filtered, and concentrated. Purification by ISCO chromatography (5 to 25% ethyl acetate:heptane) afforded 18 mg (17%) of 2-chloro-4-iodo-N-methylfuro[2,3-c]pyridin-7-amine and 44 mg (40%) of 2-chloro-4-iodo-N,N-dimethylfuro[2,3-c]pyridin-7-amine as off-white white solids.

Provenance & Evidence