Sodium Iodide → 2-Cyclopropylmethyl-5-iodo-7-methyl-2,3-dihydro-isoindol-1-one

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of 5-Bromo-7-methyl-2-cyclopropylmethyl-2,3-dihydro-isoindol-1-one (1.0 g, 3.56 mmol) in butanol (10 ml), (1R,2R)-N,N′-dimethylcyclohexane-1,2-diamine (204 mg, 1.42 mmol), copper(I) iodide (140 mg, 0.714 mmol) and sodium iodide (1.08 g, 14.3 mmol) were added. The resulting mixture was stirred at 120° C. overnight. After cooling, the mixture was diluted with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulphate, filtered, concentrated. Column chromatography (30% EtOAc/Hexanes) provided the title compound (1.07 g, 92%) as a colourless solid. 1H NMR (300 MHz, CDCl3): δ 7.65 (s, 1H), 7.59 (s, 1H), 4.42 (s, 2H), 3.46-3.44 (d, 2H), 2.70 (s, 3H), 1.04-1.02 (m, 1H), 0.61-0.57 (m, 2H), 0.34-0.31 (m, 2H)

Herkunft & Nachweise