Methyl iodide → HCID 66738428, compound

Participants

Reaction Steps

Add sodium hydride (620 mg, 26 mmol) to a solution of [2-(6-fluoro-4-iodo-pyridin-3-yloxy)-ethyl]-carbamic acid tert-butyl ester (0.33 g, 0.86 mmol) in 3 mL of DMF. Stir the mixture at RT for 1 h and add methyl iodide (0.37 g, 2.59 mmol). Stir the reaction mixture at RT overnight. Add water and extract with ethyl acetate. Wash the organic layer with saturated aqueous sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo. Purify the residue by column chromatography (20% ethyl acetate in hexane) to afford the title compound as a light yellow solid (0.13 g, 38%). 1H NMR (400 MHz, CD3CN) δ 1.45 (s, 9H), 3.08 (s, 3H), 3.59 (t, J=5.6 Hz, 2H), 4.20 (t, J=5.6 Hz, 2H), 5.07 (s, 1H), 7.38 (d, J=3.2 Hz, 1H), 7.61 (d, J=1.2 Hz, 1H).

Provenance & Evidence