2-(Dimethylamino)ethanol → 5-(2-Dimethylamino-ethoxy)-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.078 g, 0.2 mmol), 2-dimethylamino-ethanol (0.04 mL, 0.4 mmol), Pd(OAc)2 (0.001 g, 0.004 mmol), and Cs2CO3 (0.130 g, 0.4 mmol) in toluene (3 mL) was stirred at 100° C. for 24 h. Workup and silica gel column chromatography using 5:1 CHCl3-MeOH afforded 5-(2-dimethylamino-ethoxy)-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.020 g, 25%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.32 (s, 6H), 2.70 (m, 5H), 4.06 (t, 2H), 4.18 (s, 2H), 4.74 (s, 2H), 6.70 (d, 2H), 7.15-7.37 (m, 4H).

Provenance & Evidence