Sodium Iodide → HCID 90408511, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 36C (0.9 g, 1.84 mmol) and sodium iodide (3.8 g, 25.4 mmol) in acetone (15 mL) was stirred at 78° C. for 18 h. The reaction cooled to rt and filtered. The filtrate was concentrated in vacuo, taken up in DCM (10 mL) and filtered. The residual solid was washed with DCM (5 mL×2). The combined organic filtrates were concentrated in vacuo. The residual crude oil was purified by flash chromatography using a 0% to 30% gradient of EtOAc/hexane (15 min) to give the title compound (0.730 g, 1.64 mmol, 89% yield) as a white solid. 1H NMR (CDCl3) δ: 6.88 (t, J=1.7 Hz, 1H), 6.76 (ddd, J=10.1, 2.3, 1.6 Hz, 1H), 6.70 (dt, J=10.5, 2.3 Hz, 1H), 5.41 (t, J=3.1 Hz, 1H), 3.96-3.85 (m, 3H), 3.68-3.60 (m, 1H), 3.07 (s, 2H), 2.10-1.95 (m, 5H), 1.89-1.58 (m, 9H); 19F NMR (CDCl3) δ: −111.9 (s).

Provenance & Evidence