N,N'-Dimethylethylenediamine → HCID 68504614, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the bromide from Step E (0.4 g, 1.1 mmol, slightly impure) and 2-hydroxy-pyridine (0.13 g, 1.37 mmol) from Step E in 1,4-dioxane (1.4 mL) were added N,N′-dimethylethylenediamine (50 μL, 0.46 mmol) and potassium phosphate (0.48 g, 2.30 mmol). The mixture was purged with argon for ˜10 minutes, and copper (I) iodide (40 mg, 0.2 mmol) was added to it. The reaction was heated at 110° C. for 12 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane, washed with water and brine, dried over sodium sulfate, filtered and concentrated to give the crude product. Purification by preparative thin layer chromatography (90:9:1 dichloromethane/methanol/concentrated ammonium hydroxide) twice gave the desired product (144 mg, 36%) as an off-white foam: 1H NMR (CDCl3, 300 MHz) δ 7.45-7.26 (m, 3H), 7.25-7.21 (m, 2H), 6.95 (t, J=8.6 Hz, 2H), 6.88-6.83 (m, 2H), 6.64 (d, J=9.2 Hz, 1H), 6.30-6.25 (m, 1H), 5.36-5.30 (m, 1H), 4.05-3.83 (m, 2H), 3.35-3.20 (m, 1H), 3.10-3.00 (m, 1H), 2.37 (s, 3H), 2.20-2.13 (m, 2H).

Provenance & Evidence