Tetrahydrofuran → HCID 57933023, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. mixture of 2-methylfuran (0.18 mL, 2.04 mmol) and Et2O (2 mL) is added 1.6 M t-Bu-Li in hexane (1.30 mL, 2.14 mmol). The mixture is heated at a reflux for 30 minutes, cooled to 0° C., and 0.5 M ZnCl2 in THF (4.3 mL, 2.14 mmol) is added and the solution warmed to ambient temperature. 3-(5-bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.40 g, 1.02 mmol) and PdCl2(dppf) (0.037 g, 0.051 mmol) is added and mixture is stirred at 65° C. overnight, diluted with EtOAc (30 mL), washed with 10% citric acid (15 mL), water (15 mL), brine (15 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO column chromatography (20% EtOAc/hexane gradient) furnish the title compound (0.20 g, 0.51 mmol, 50%). 1H NMR (CDCl3), δ 0.89 (t, J=7.5 Hz, 6H), 1.74-1.92 (m, 4H), 2.12 (s, 3H), 2.35 (s, 3H), 2.48 (s, 3H), 2.51 (s, 3H), 3.29-3.38 (m, 1H), 6.62 (dd, J=3.1, 0.9 Hz, 1H), 6.40 (d, J=3.1 Hz, 1H), 6.66 (s, 1H), 7.12 (s, 1H). LC/MS (m/z): calcd. for C23H27N3OS (M+H)+: 394.3; found: 394.2.

Provenance & Evidence