Iodine → HCID 118274112, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 41C (26.6 g, 65.3 mmol) in tetrahydrofuran (326 mL) at −75° C. under nitrogen was added lithium diisopropylamide (49.0 mL, 98 mmol) dropwise. A solution of iodine (33.1 g, 131 mmol) in 250 mL tetrahydrofuran was added dropwise and the mixture was stirred at −75° C. for 2 hours. The reaction was quenched with saturated aqueous sodium thiosulfate and extracted with ethyl acetate (twice). The combined organics were dried over magnesium sulfate, filtered and concentrated. The residue was slurried in hot 40% ethyl acetate in heptanes, cooled to room temperature and filtered and dried in vacuo to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.39 (d, J=5.3 Hz, 1H), 7.97 (d, J=8.4 Hz, 2H), 7.71 (d, J=10.3 Hz, 1H), 7.57 (d, J=5.4 Hz, 1H), 7.42 (d, J=8.3 Hz, 2H), 7.33-7.22 (m, 2H), 4.01 (s, 2H), 2.89 (s, 3H), 2.32 (s, 3H). MS (ESI+) m/z 534.0 (M+H)+.

Provenance & Evidence