Nitrogen → HCID 57932923, compound

Participants

Reaction Conditions

Reaction Steps

A slurry of 2,6-dimethyl-8-(1-propyl-butyl)-imidazo[1,2-b]pyridazine (below) (0.30 g, 1.22 mmol), 5-(5-bromo-4-chloro-thiophen-2-yl)-1-methyl-[1,2,4]triazole (below) (0.41 g, 1.47 mmol), KOAc (0.60 g, 6.11 mmol), TBABr (0.39 g, 1.22 mmol), and NMP (3 mL) is de-gassed with N2 for 30 minutes. Pd(OAc)2 (0.014 g, 0.061 mmol) and TDBPP (0.040 g, 0.061 mmol) are added and the solution heated at 125° C. for 2.5 hours. The solution is diluted with EtOAc (50 mL), washed with water (3×50 mL), brine (50 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO flash chromatography (20%-40% EtOAc gradient) furnish the title compound (0.30 g, 0.68 mmol, 56%). 1H NMR (CDCl3) δ 0.89 (t, J=7.4 Hz, 6H), 1.14-1.39 (m, 4H), 1.76 (q, J=16.3, 7.7 Hz, 4H), 2.51 (s, 3H), 2.52 (s, 3H), 3.41-3.50 (m, 1H), 4.15 (s, 3H), 6.73 (s, 1H), 7.48 (s, 1H), 7.90 (s, 1H). LC/MS (m/z): calcd. for C22H27ClN6S (M+H)+: 443.2; found: 443.3.

Provenance & Evidence