Iodine → HCID 72721600, compound

Participants

Reaction Steps

To a suspension of Example 8 (0.10 g) in a mixture of acetic acid (2 mL) and phosphinic acid (0.1 mL) was added iodine (0.05 g). The mixture was heated at 100° C. for 1.5 h before the addition of extra iodine (8 mg) and phosphinic acid (0.02 mL). Heating was continued for 4 h and then the mixture was cooled to room temperature overnight. The mixture was concentrated in vacuo and the residue was partitioned between DCM (20 mL) and saturated aqueous NaHCO3 solution (20 mL). The organic phase was separated, dried (Na2SO4), filtered and concentrated in vacuo. The resulting crude product was purified by preparative HPLC to give the title compound (0.025 g) as a white solid. δH (400 MHz, DMSO-d6) 7.21 (t, 1H, J 1.2 Hz), 6.95 (s, 1H), 6.78 (d, 1H, J 0.6 Hz), 6.55 (m, 2H), 6.46 (d, 1H, J 8.5 Hz), 6.27 (dd, 1H, J 8.5, 2.5 Hz), 5.93 (d, 1H, J 2.5 Hz), 3.45 (s, 2H), 2.91 (s, 3H), 1.36 (s, 3H). MH+ 372.

Provenance & Evidence