Iodine → HCID 131735518, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 14G (310.0 mg, 0.837 mmol) in tetrahydrofuran (8 mL) at −78° C. was added 2M lithium diisopropylamide (1.255 mL, 2.51 mmol) in tetrahydrofuran/heptane/ethylbenzene dropwise. After 60 minutes, a solution of iodine (531 mg, 2.092 mmol) in tetrahydrofuran (3 mL) was cannulated into the reaction mixture and the mixture was stirred at −78° C. for 2 hours. The mixture was quenched with aqueous sodium thiosulfate and extracted with ethyl acetate (twice). The combined organic layers were dried over magnesium sulfate, filtered, concentrated, and purified on silica using the ISCO Companion flash system eluting with heptanes/ethyl acetate (9:1 to 8:2) to provide the title compound. MS (ESI+) m/z 496.8 (M+H)+.

Provenance & Evidence