N-Iodosuccinimide → HCID 67430914, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-methyl-2-(1-(((benzyloxy)carbonyl)amino)ethyl)imidazo[1,2-a]pyridine-5-carboxylate (5.5 g, 7.93 mmol) in acetonitrile (50 mL) was added N-iodosuccinimide (2.3 g, 10.3 mmol) at 25° C. The reaction mixture was stirred at 25° C. overnight. After completion of the reaction, the mixture was diluted with water and extracted with EtOAc. The organic layer was washed with satd. sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography using silica gel (100-200 mesh) and 0-50% EtOAc in hexane to provide (S)-methyl 2-(1-(((benzyloxy)carbonyl)amino)ethyl)-3-iodoimidazo[1,2-a]pyridine-5-carboxylate: 1H NMR (CDCl3, 400 MHz) δ 1.547 (d, J=6.8 Hz, 3H), 4.048 (s, 3H), 5.067-5.200 (m, 3H), 5.805 (d, J=7.2 Hz, 1H), 7.229-7.260 (m, 2H), 7.292-7.350 (m, 5H), 7.675-7.708 (m, 1H); LC-MS (ESI) m/z 479.9 [M+H]+.

Provenance & Evidence