Methyl iodide → HCID 59596237, compound

Participants

Reaction Steps

To a solution of [3,3-bis-(4-hydroxy-phenyl)-3H-isoindol-1-yl]-carbamic acid tert-butyl ester (Scheme #2, C) (5.0 g, 12.0 mmol) and cesium carbonate (3.9 mL, 12.0 mmol) in N,N-dimethyl formamide (100 mL) was added iodomethane (0.7 mL, 11.4 mmol) in N,N-dimethyl formamide (3 mL) and the mixture stirred at ambient temperature for 18 hours. The N,N-dimethyl formamide was removed under reduced pressure to yield an amber syrup. To this was added ethyl acetate (250 mL) and the mixture stirred vigorously for 0.5 h. The insolubles were filtered and the filtrate concentrated under reduced pressure to yield a tan solid. The crude compound was purified using flash chromatography (silica; 90:10 dichloromethane:ethyl acetate) to give the title compound as a white solid (2.11 g, 34%). 1H NMR (300 MHz, DMSO-d6) δ 7.83 (d, J=7.5 Hz, 1 H), 7.64 (t, J=7.3 Hz, 1 H), 7.55-7.49 (m, 2 H), 7.16 (d, J=8.8 Hz, 2 H), 7.04 (d, J=8.6 Hz, 2 H), 6.89 (d, J=8.8 Hz, 2 H), 6.71 (d, J=8.7 Hz, 2 H), 3.71 (d, J=8.3 Hz, 3 H), 1.46 (s, 9 H); MS (APCI+) m/z 430 [M+1]+; tR=2.20 min.

Provenance & Evidence