Phthalimide → HCID 71272451, compound

Participants

Reaction Steps

To a solution of isoindoline-1,3-dione (3.83 g, 20.0 mmol), in dry DMF (70 mL) at 0° C. under argon was added NaH (1.04 g, 26 mmol). The resultant mixture was stirred at RT for 30 min. A solution of 284 (9.8 g, 26 mmol) in dry DMF (30 mL) was added and the mixture was stirred at RT for 4 h. The mixture was concentrated in vacuo and purified by SiO2 chromatography to afford 10 g (86%) of 2-(1-(1-tosyl-1H-indol-4-yl)ethyl)isoindoline-1,3-dione (286) as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 7.87-7.81 (m, 8H), 7.48 (d, J=7.6 Hz, 1H), 7.38-7.33 (m, 3H), 6.82 (d, J=3.6 Hz, 1H), 5.77-5.74 (m, 1H), 2.29 (s, 3H), 1.84 (d, J=6.8 Hz, 3H).

Provenance & Evidence