2-Chloromethyl-imidazo(1,2-A)pyridine → 2-(imidazo[1,2-a]pyridin-2-ylmethyl)-1H-isoindole-1,3(2H)-dione

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Reaction Conditions

Reaction Steps

1.5 g (9 mmol) of 2-(chloromethyl)imidazo[1,2-a]pyridine were solubilised in 55 ml of dimethylformamide with magnetic stirring, 1.834 g (9.9 mmol) of potassium phthalimide were added portion wise and then the mixture was stirred at 60° C. for 2 h. The obtained solid was isolated by filtration, washed with 30 ml of diisopropyl ether and dried in a vacuum bell jar in order to obtain 1.81 g (yield=67%) of 2-(imidazo[1,2-a]pyridin-2-ylmethyl)isoindoline-1,3-dione as a white solid. LC-MS: m/z=278 (MH+); UV purity at 254 nm=93%. 1H NMR (300 MHz, DMSO) δ 8.45 (d, J=6.8 Hz, 1H), 7.96-7.67 (m, 5H), 7.45 (dd, J=9.1, 0.5 Hz, 1H), 7.33-7.14 (m, 1H), 6.84 (td, J=6.8, 1.1 Hz, 1H), 4.88 (s, 2H).

Provenance & Evidence