Iodine → {1-[4-(1-Methyl-6-oxo-8-phenyl-1,6-dihydro-chromeno[7,8-d]imidazol-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a stirred solution of {1-[4-(7-amino-8-methylamino-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (95 mg, 0.19 mmol) in acetonitrile (3 mL) was added trimethylorthoformate (24 μL, 0.22 mmol) and iodine (5 mg, 0.02 mmol) at RT. After 1 hour, the reaction mixture was quenched with Na2S2O3. The resulting mixture was extracted with ethyl acetate (2×30 mL) and the combined organics washed with brine, dried (Na2SO4) and the solvents were removed in vacuo. The resulting residue was subjected to flash chromatography (SiO2, ethyl acetate) to give the title compound as a white solid (67 mg, 68%). LCMS (Method G): RT=3.63 min, [M+H]+=522.

Provenance & Evidence