Potassium Carbonate → HCID 67985009, compound

Participants

Reaction Steps

N-(3-(4,5-dihydro-1H-imidazol-2-yl)-2-(4-fluorophenyl)-5-isopropoxybenzofuran-6-yl)-N-(4-methoxybenzyl)methanesulfonamide (0.54 g, 0.98 mmol) was dissolved in dimethylsulfoxide (5 mL) and was treated with potassium carbonate (0.15 g, 1.08 mmol) and iodobenzene diacetate (0.35 g, 1.08 mmol). The initially yellow solution changed to a reddish-brown solution within 15 minutes of iodobenzene diacetate addition. The reaction mixture was stirred for one hour at room temperature. The reaction mixture was stirred with 50 mL ethyl acetate and 50 mL 10% aqueous sodium bicarbonate for 20 minutes, the layers were separated and the aqueous layer was extracted with 50 mL additional ethyl acetate. The combined organic extracts were washed with 10% aqueous sodium chloride, dried over anhydrous sodium sulfate(s), and filtered. The solvent was removed in vacuo leaving an orange oily residue, which was purified by reverse phase HPLC yielding an off-white solid. 40 mg, 7.4%. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.39 (d, 6H) 3.13 (s, 3H) 3.67 (s, 3H) 4.37-5.02 (m, 3H) 6.73-6.92 (m, 2H) 7.06-7.22 (m, 4H) 7.22-7.41 (m, 4H) 7.79-7.98 (m, 2H) 12.37 (s, 1H); MS (ESI+) m/z 550.2 (M+H)+, MS (ESI−) m/z 548.1.

Provenance & Evidence