反应详情

A mixture of 5-(4-bromophenyl)-5-(carboxymethyl)-5H-imidazo[2,1-a]isoindol-1-ium trifluoroacetate (1.27 g), Et3N (0.989 mL) and 4 Angstrom powdered molecular sieves in t-BuOH (10 mL) was stirred for 20 minutes at room temperature. Diphenylphosphorylazide was then added to this mixture and heated at 95° C. overnight. After cooling to room temperature the reaction mixture was filtered through a pad of celite. The celite pad was washed thoroughly with CH2Cl2, combined washings and filtrate were concentrated. The residue was dissolved in CH2Cl2 and the organic layer was washed with half-saturated aqueous NaHCO3 solution (1×), dried over Na2SO4 and concentrated. Flash chromatography using a linear gradient of 3% EtOAc/0% MeOH to 50% EtOAc/2% MeOH in hexanes afforded title compound as a white solid. Mass. found (M+H)+, 442.0.

1. temperatureheated at 95° C. overnight
2. temperatureAfter cooling to room temperature the reaction mixture
3. filtrationwas filtered through a pad of celite
4. washThe celite pad was washed thoroughly with CH2Cl2
5. concentrationwere concentrated
6. dissolutionThe residue was dissolved in CH2Cl2
7. washthe organic layer was washed with half-saturated aqueous NaHCO3 solution (1×)
8. dry with materialdried over Na2SO4
9. concentrationconcentrated