Phthalimide → 2-((1-(4-fluorophenyl)-2-((2,3,6-trifluoro benzyl)thio)-1H-imidazol-5-yl)methyl)isoindoline-1,3-dione

Participants

Reaction Steps

Phthalimide (783 mg, 5.32 mmol), di-tert-butylazodicarboxylate (1.23 g, 5.32 mmol) and triphenyl phosphine (1.4 g, 5.32 mmol) were added to a solution of (1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazol-5-yl)methanol (28) (980 mg, 2.66 mmol) in THF (30 mL) and the reaction was stirred overnight at room temperature. An additional equivalent of phthalimide, di-tert-butylazodicarboxylate and triphenyl phosphine was added and stirred overnight. Water and ethyl acetate were added and the layers were separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-100% EtOAc in hexanes) to afford 2-((1-(4-fluorophenyl)-2-((2,3,6-trifluoro benzyl)thio)-1H-imidazol-5-yl)methyl)isoindoline-1,3-dione (29) as an oil.

Provenance & Evidence