Tetrahydrofuran → HCID 57932961, compound

Participants

Reaction Steps

To a −78° C. solution of dimethyl-(4-methyl-thiophen-3-yl)-amine (0.43 g, 3.06 mmol) and THF (5 mL) is added 1.6 M n-BuLi (1.91 mL, 3.06 mmol). The solution is stirred for 1 hour, then 0.5 M ZnCl2 (6.1 mL, 3.06 mmol) is added and the solution warmed to ambient temperature. After 30 minutes 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.70 g, 2.04 mmol) and PdCl2(dppf) (0.075 g, 0.10 mmol) is added and the solution heated at 65° C. overnight. The solution is diluted with EtOAc (35 mL), washed with sat. NH4Cl (30 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO flash chromatography (15%-30% EtOAc gradient) furnish the title compound (0.13 g, 0.36 mmol, 18%). 1H NMR (CDCl3) δ 0.86 (t, J=7.5 Hz, 6H), 1.72-1.90 (m, 4H), 2.03 (s, 3H), 2.45 (s, 3H), 2.50 (s, 3H), 2.77 (s, 6H), 3.28-3.37 (m, 1H), 6.63 (s, 1H), 6.65 (s, 1H). LC/MS (m/z): calcd. for C20H28N4S (M+H)+: 357.2; found: 357.2

Provenance & Evidence