Iodide Ion → HCID 69507850, compound

Participants

Reaction Steps

The tributyltin reagent from Example 1C (665 μL, 1.83 mmol) was added under nitrogen atmosphere to a mixture of alcohol from Example 1B (433 mg, 1.66 mmol), tris(dibenzylideneacetone)-dipalladium(0) (76 mg, 0.083 mmol), tri-2-furylphosphine (39 mg, 0.166 mmol), and cupper(I) iodide (32 mg, 0.166 mmol) in DMF (7 mL). The reaction mixture was stirred at ambient temperature for 30 minutes. Aqueous potassium fluoride was added to the mixture and the resulting suspension was filtered through celite and washed with ethyl acetate. The filtrate was taken up in ethyl acetate and water. The organic phase was washed with brine (×3), dried (MgSO4), filtered and concentrated under reduced pressure and purified by flash chromatography on silica gel with hexane/ethyl acetate (1:1) to provide the titled compound (353 mg). MS (ESI(+)) m/e 291 (M+18)+; 1H NMR (500 MHz, DMSO-d6) δ 8.05(t, J=1.7 Hz, 1H), 7.80 (dt, J1=1.7 Hz, J2=7.5 Hz, 1H), 7.60 (dt, J1=1.7 Hz, J2=7.5 Hz, 1H), 7.57 (s, 1H), 7.51(t, J=7.5 Hz, 1H), 6.63–6.59 (m, 2H), 4.94 (t, J=5.4 Hz, 1H), 4.41 (q, J=7.1 Hz, 2H), 4.19–4.14(m, 2H), 1.35 (t, J=7.1 Hz, 3H).

Provenance & Evidence