Nitrogen → 2,6-Dimethyl-3-[3-methyl-5-(6-methyl-pyridin-2-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazine

Participants

Reaction Conditions

Reaction Steps

A solution of 2,6-dimethyl-imidazo[1,2-b]pyridazine (below) (0.50 g, 3.39 mmol), 2-(5-bromo-4-methyl-thiophen-2-yl)-6-methyl-pyridine (1.00 g, 3.73 mmol), Cs2CO3 (2.32 g, 7.13 mmol) and DMF (5 mL) is de-gassed for 15 minutes with N2. Pd2(dba)3 (0.15 g, 0.16 mmol) and PPh3 (0.17 g, 0.65 mmol) is added and the solution is heated at 130° C. overnight. The solution is diluted with CH2Cl2 (30 mL) washed with water (2×25 mL), brine (25 mL) dried over MgSO4, filtered and concentrated. The residue is purified by ISCO column chromatography (100% EtOAc), followed by recrystallization from acetonitrile/water furnish the title compound (0.45 g, 1.35 mmol, 39%). 1H NMR (CDCl3), δ 2.13 (s, 3H), 2.50 (s, 3H), 2.53 (s, 3H), 2.57 (s, 3H), 6.90 (d, J=9.2 Hz, 1H), 7.01 (d, J=7.5 Hz, 1H), 7.46 (d, J=8.0 Hz, 1H), 7.52 (s, 1H), 7.56 (dd, J=8.0, 7.5 Hz, 1H), 7.77 (d, J=9.2 Hz, 1H). LC/MS (m/z): calcd. for C19H18N4S (M+H)+: 335.1; found: 335.1.

Provenance & Evidence