N-Iodosuccinimide → HCID 86725336, compound

Participants

Reaction Steps

Into a 100 ml flask, the product of step (e) (1.03 g, 3.05 mmol) dissolved in TFA (10 ml) was added. To this stirred solution, NIS (828 mg, 3.68 mmol) was added. The reaction mixture was stirred at room temperature for 45 minutes, then carefully poured over ice-cold saturated aqueous NaHCO3 (200 ml). The aqueous mixture was extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the crude product. Purification by silica-gel chromatography (gradient elution: 0 to 30% EtOAc in hexanes) gave the sub-title compound as a yellow solid (166 mg). 1H NMR (300 MHz, CDCl3) δ 7.29 (s, 1H); 5.99 (s, 1H); 3.76-3.67 (m, 4H); 3.33-3.30 (m, 2H); 3.00-2.96 (m, 2H); MS: ESI (positive): 464, 466 (M+H).

Provenance & Evidence