HCID 11374420, compound → HCID 11175601, compound

Participants

Reaction Steps

A mixture of 2-[4-(2-methoxyethoxy)phenyl]-3-iodo-6-propoxyimidazo[1,2-b]pyridazine (100 mg, 0.22 mmol), cuprous cyanide (22 mg, 0.24 mmol) and N,N-dimethylformamide (2 mL) was heated at 80° for 22 hours. More CuCN (10 mg) was added and the mixture heated at 100° for 29 hours. Aqueous ferric chloride solution (5%, acidified with HCl) (7 mL) was added and the resulting mixture heated at 60° for 30 minutes. The resulting suspension was filtered and the collected solid washed with saturated, aqueous sodium bicarbonate solution, water (twice) and air-dried overnight. The beige coloured solid was radially chromatographed on silica gel. Elution with 0-1% methanol in dichloromethane provided Compound 110 (50 mg, 64%) as a brilliant white solid. 1H n.m.r. (CDCl3) δ 1.06, t, J=7.4 Hz, 3H; 1.76-1.96, m, 2H; 3.47, s, 3H; 3.74-3.82, m, 2H; 4.15-4.22, m, 2H; 4.37, t, J=6.6 Hz, 2H; 6.88, d, J=9.5 Hz, 1H; 7.04, d, J=8.8 Hz, 2H; 7.82, d, J=9.5 Hz, 1H; 8.09, d, J=8.7 Hz, 2H. Mass spectrum (APCI+) m/z 353 (M+H, 100%). Further elution afforded recovered starting material (21 mg, 21%).

Provenance & Evidence