Potassium Carbonate → HCID 20740830, compound

Participants

Reaction Conditions

Reaction Steps

An oven-dried resealable Schlenk tube was charged with CuI (40 mg, 0.210 mmol), K2CO3 (850 mg, 6.15 mmol), evacuated and backfilled with argon. trans-1,2-Cyclohexanediamine (240 μL, 2.00 mmol) and 5-iodo-m-xylene (900 μL, 6.24 mmol) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 100° C. for 23 h. The resulting purple-blue suspension was cooled to room temperature and filtered through a 2×1 cm pad of Celite eluting with 50 mL of dichloromethane. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×20 cm; dichloromethane saturated with aq NH3-methanol 40:1; 15 mL fractions). Fractions 9–13 provided 178 mg (41% yield) of the product as a tan solid. 1H NMR (400 MHz, CDCl3): δ 6.39 (s, 1H), 6.34 (s, 2H), 3.36 (br s, 1H), 3.03–2.92 (m, 1H), 2.56–2.46 (m, 1H), 2.25 (s, 6H), 2.20–2.10 (m, 1H), 2.08–1.95 (m, 1H), 1.83–1.70 (m, 2H), 1.55–1.20 (m, 5H), 1.10–1.00 (m, 1H).

Provenance & Evidence