Potassium Carbonate → N-(4-{4-(5-(2-Methoxyethoxy)pyrazin-2-ylthio)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 25-1 (3.00 g, 6.89 mmol), 5-(2-methoxyethoxy)pyrazine-2-thiol (27-2, 2.57 g, 13.8 mmol), copper iodide (66.0 mg, 0.35 mmol), and potassium carbonate (2.86 g, 20.7 mmol) in 13.8 mL of DMF was stirred at 100° C. for 7.0 h. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (EtOAc:hexnaes=2:1 as eluant) to give N-(4-{4-(5-(2-methoxyethoxy)pyrazin-2-ylthio)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamide (27, 2.00 g) as light yellow solids in 59% yield: 1H NMR (500 MHz, CDCl3) δ 8.75 (d, J=4.0 Hz, 2 H), 8.19 (d, J=1.0 Hz, 1 H), 8.00 (d, J=1.0 Hz, 1H), 7.63 (d, J=5.0 Hz, 2 H), 6.96 (s, 1 H), 6.79 (s, 2 H), 4.44 (t, J=4.5 Hz, 2 H), 3.72 (t, J=4.5 Hz, 2 H), 3.41 (s, 3 H), 1.95 (s, 6 H). ESI-MS: m/z 494.2 (M+H)+.

Provenance & Evidence