Sodium Hydroxide → HCID 11269675, compound

Participants

Reaction Steps

2-[4-(2-Methoxyethoxy)phenyl]-3-iodo-6-propoxyimidazo[1,2-b]pyridazine (100 mg, 0.22 mmol) was dissolved with stirring in 1,2-dimethoxyethane (2.5 mL) under an atmosphere of nitrogen. Phenylboronic acid (30 mg, 0.24 mmol) was added followed by tetrakis(triphenylphosphine)-palladium(0) (20 mg). A solution of sodium hydroxide (18 mg, 0.44 mmol) in water (1 mL) was added. The resulting mixture was heated at 70° for 1 hour then cooled and partitioned between dichloromethane and water. The aqueous layer was extracted with dichloromethane and the combined organics dried and evaporated. The cream coloured solid residue was radially chromatographed on silica gel. Elution with 0-3% methanol in dichloromethane provided Compound 97 (74 mg) as a white solid. 1H n.m.r. (CDCl3) δ 1.00, t, J=7.3 Hz, 3H; 1.74-1.86, m, 2H; 3.45, s, 3H; 3.75, t, J=4.3 Hz, 2H; 4.13, t, J=4.3 Hz, 2H; 4.18, t, J=6.3 Hz, 2H; 6.70, d, J=9.5 Hz, 1H; 6.88, d, J=8.4 Hz, 2H; 7.35-7.47, m, 3H; 7.57, d, J=8.3 Hz 2H; 7.62, d, J=6.8 Hz, 2H; 7.82, d, J=9.3 Hz, 1H. Mass spectrum (APCI+) m/z 404 (M+H, 100%).

Provenance & Evidence