Dimethylformamide → 6-(2,4-Difluorophenyl)-5-iodoimidazo[2,1-b]oxazole

Participants

Reaction Steps

A solution of 6-(2,4-difluorophenyl)imidazo[2,1-b]oxazole (30.0 g, 136 mmol; Example #8, step B), NIS (31.6 g, 140 mmol), and DMF (350 mL) was stirred at ambient temperature. After about 1 h, the reaction was poured into water (2 L) and the resulting precipitate was filtered and washed with additional water. The brown solid was dissolved in DCM and washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to dryness. The solid was dissolved in DCM, filtered through Florosil® and then concentrated under reduced pressure to a volume of about 0.5 L. The organic layer was washed with 5% aqueous NaS2O3, dried over MgSO4, filtered, and concentrated under reduced pressure to dryness to give the title compound as a yellow solid (34.5 g, 73%): LC/MS (Table 1, Method a) Rt=2.67 min; MS m/z: 346.9 (M+H)+.

Provenance & Evidence