Ethyl bromopyruvate → Ethyl 6-iodoimidazo[1,2-a]pyridine-2-carboxylate

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Reaction Steps

Add 3-bromo-2-oxo-propionic acid ethyl ester (1.75 g, 9.09 mmol) to a solution of 2-amino-5-iodo pyridine (Tetrahedron 2002, 58, 2885-2890; 1.0 g, 4.54 mmol) in acetonitrile (100 ml). Reflux for 12 h, concentrate to ˜30 ml, and dilute with saturated aqueous sodium bicarbonate. Extract into dichloromethane, combine organic extracts, dry over anhydrous magnesium sulfate, and concentrate. Titurate the residue in diethyl ether and filter to give 0.8 g (56%) of the subtitled compound as an off-white solid. TOF MS ES+ exact mass calculated for C10H91N2O2 (p+1): m/z=316.9787; Found: 316.9784. 1H NMR (400 MHz, DMSO-d6) δ 8.97 (m, 1H), 8.46 (s, 1H), 7.57-7.49 (m, 2H), 4.32 (q, T 7.0 Hz, 2 Hz), 1.33 (t, J=7.0 Hz, 3H).

Provenance & Evidence