Hydrochloric Acid → HCID 57752696, compound

Participants

Reaction Steps

4-Methoxy-3-methyl-benzofuran (240 mg, 1.50 mmol) added to THF (6 ml) and cooled to −72° C. n-Butyl lithium (1.0 ml, 1.60 mmol) added and stirred for 5 minutes, warmed to ambient temperature for 10 minutes and cooled again to −72° C. Zinc chloride (0.5 N in THF, 3.2 ml, 1.6 mmol) added, stirred for 5 minutes then warmed to ambient temperature and stirred for 10 minutes. 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (240 mg, 0.69 mmol) and PdCl2(dppf)-CH2Cl2 complex (Aldrich, 64 mg, 0.08 mmol) are added. The mixture is heated to 60° C. for 4 hrs, cooled to ambient temperature, added to HCl (1N) and extracted twice with EtOAc. The combined organic extracts are dried over Na2SO4, filtered and concentrated. The crude product is purified by chromatography using a hexane-ethyl acetate gradient (100% hexane to 30% ethyl acetate in hexane) to give the title compound (54 mg, 21% yield). ES-MS (m/z): calc'd for C23H27N3O2: 377.5. found 378.1 (M+H)+1H NMR (400 mHz, CDCl3): δ 7.27 (t, 1H), 7.18 (d, 1H), 6.74 (s, 1H), 6.70 (d, 1H), 3.99 (s, 3H), 3.39 (bs, 1H), 2.55 (s, 3H), 2.54 (s, 3H), 2.41 (s, 3H), 1.87 (m, 4H), 0.91 (t, 6H) ppm.

Provenance & Evidence