Hexane → HCID 57933065, compound

Participants

Reaction Conditions

Reaction Steps

To a −78° C. solution of oxazole (0.14 g, 2.04 mmol) and THF (3 mL) is added 1.6 M t-Bu-Li in hexane (1.32 mL, 2.14 mmol). The mixture is stirred at −78° C. for 15 minutes. 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 (20 mL), water (20 mL), brine (20 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO column chromatography (20% EtOAc/hexane gradient) and is chromatographed (50×250 C18 Symmetry column, 20-70% water: 0.1% TFA/ACN: 0.1% TFA gradient) to furnish the title compound (0.020 g, 0.053 mmol, 5%). 1H NMR (CDCl3), δ 0.89 (t, J=7.5 Hz, 6H), 1.75-1.93 (m, 4H), 2.17 (s, 3H), 2.49 (s, 3H), 2.51 (s, 3H), 3.29-3.38 (m, 1H), 6.69 (s, 1H), 7.19 (s, 1H), 7.59 (s, 1H), 7.65 (s, 1H). LC/MS (m/z): calcd. for C21H24N4OS (M+H)+: 381.3; found: 381.1.

Provenance & Evidence