Propylamine → HCID 78322292, compound

Participants

Reaction Steps

n-Propylamine (148 mg, 2.5 mol) was added to a solution of ethyl 3-(4-chloro-3-fluorophenyl)-3H-imidazo[4,5-b]pyridine-2-carboxylate (C13) (80 mg, 0.25 mmol) in ethanol (5 mL) and the reaction mixture was stirred at room temperature for 18 hours. After concentration under reduced pressure, the residue was purified by preparative thin layer chromatography on silica gel (Eluent: 1:1 petroleum ether/ethyl acetate) to provide the product as a pale yellow solid. Yield: 28 mg, 84 μmol, 34%. LCMS m/z 332.9 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.43 (dd, J=4.8, 1.4 Hz, 1H), 8.26 (dd, J=8.2, 1.5 Hz, 1H), 7.67 (dd, J=8.4, 8.2 Hz, 1H), 7.45-7.50 (m, 2H), 7.30 (ddd, J=8.5, 2.3, 1.2 Hz, 1H), 3.28-3.34 (m, 2H, assumed; partially obscured by solvent peak), 1.58-1.68 (m, 2H), 0.96 (t, J=7.4 Hz, 3H).

Provenance & Evidence