Nitrogen → 3-[3-chloro-5-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiophen-2-yl]-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(1-ethyl-propyl)-2-methoxy-6-methyl-pyrrolo[1,2-b]pyridazine (74.8 mg, 0.32 mmol), 5-(5-bromo-4-chloro-thiophen-2-yl)-1-methyl-1H-[1,2,4]triazole (107.5 mg, 0.38 mmol), TDBPP (10.4 mg, 0.016 mmol), tetrabutylammonium bromide (103.0 mg, 0.32 mmol), KOAc (158 mg, 1.61 mmol) in NMP (15 mL) is purged with N2 for 5 min. Pd(OAc)2 (3.6 mg, 0.016 mmol) is added and the resulting mixture is stirred at 125° C. for 6 h. The reaction is cooled to rt, and diluted with EtOAc (10 mL); filtered through silica gel; washed with EtOAc (3×30 mL). The filtrate is washed with H2O (3×30 m); dried with Na2SO4, filtered and concentrated. Purification of the crude material by silica gel chromatography gives the title compound (0.1062 g, 0.2469 mmol, 77%). 1H NMR (CDCl3): δ. 0.89 (t, J=7.6 Hz, 6H), 1.75-1.90 (m, 4H), 2.52 (s, 3H), 3.22-3.38 (m, 1H), 3.93 (s, 3H), 4.15 (s, 3H), 6.52 (s, 1H), 7.48 (s, 1H), 7.91 (s, 1H). ES-MS (m/z): calcd for C20H23ClN6OS (M+H)+: 431.9; found: 431.3.

Provenance & Evidence