Ethyl Acetate → HCID 57932941, compound

Participants

Reaction Steps

A solution of 3-(5-bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (1.00 g, 2.66 mmol) in CH3OH (12 mL), DMSO (18 mL), Et3N (2.0 mL) with Pd(OAc)2 (0.12 g, 0.538 mmol), dppf (0.937 g, 1.69 mmol) is reacted at CO atmosphere (100 psi) at 80° C. for 24 h. The reaction mixture is diluted with EtOAc (200 mL), washed with 0.1 M HCl (2×50 mL), brine (50 mL); dried with Na2SO4; filtered through silica gel and eluted with excess EtOAc. Purification of the crude material by chromatography gives the title compound (0.79 g, 2.12 mmol, 80%). 1H NMR (CDCl3): δ 0.89 (t, J=7.7 Hz, 6H), 1.75-1.93 (m, 4H), 2.15 (s, 3H), 2.50 (s, 3H), 2.53 (s, 3H), 3.32-3.42 (m, 1H), 3.91 (s, 3H), 6.72 (s, 1H), 7.73 (s, 1H). ES-MS (m/z): calcd for C20H25N3O2S (M+H)+: 372.5; found: 372.2.

Provenance & Evidence