Potassium Iodide → HCID 70983865, compound

Participants

Reaction Steps

Tert-butyl 2-(di(pyridine-2-yl)amino)acetate was prepared with modification to Kirin et al., 2007, J. Inorg. Chem., 3686-3694, the entire contents of which are incorporated herein by reference. Potassium hydroxide (3.0 g, 53.6 mmol, 4.6 equiv) was added to a solution of 2,2′-dipyridylamine (2.0 g, 11.7 mmol) in 40 ml DMSO and stirred at room temperature for 16 hours (h). Potassium iodide (200 mg, 1.2 mmol, 0.1 equiv) and tert-butyl bromoacetate (4 ml, 2.3 equiv) were added to the mixture, and the reaction was stirred for 2 h at room temperature. The reaction mixture was extracted with diethyl ether (3×50 ml). The organic fractions were combined and dried over magnesium sulfate, and the solvent was removed by rotary evaporation. The crude product was isolated by flash chromatography (SiO2, hexane/ethyl acetate=8:2) to give a yellow oil. DPA was obtained (Yield: 2.92 g (88%)), and confirmed by 1H NMR (CDCl3, 300 MHz): δ 8.33 (ddd, J=5.0, 1.9, 0.9 Hz; 2H), 7.53 (m, 2H), 7.23 (m, 2H), 6.88 (ddd, J=7.2, 5.0, 0.9 Hz; 2H), 4.84 (s, 2H), 1.42 (s, 9H). ESI-MS (cation): 286 m/z (M+H+) obsd, 286 m/z calcd.

Provenance & Evidence