Water → 2-(3,4-Dimethoxy-phenyl)-5-(3-fluoro-4-methanesulfonyl-phenyl)-6-methyl-imidazo[2,1-b][1,3,4]thiadiazole

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Reaction Steps

To a suspension of 2-(3,4-dimethoxy-phenyl)-5-iodo-6-methyl-imidazo[2,1-b][1,3,4]thiadiazole (0.035 g, 0.087 mmol, 1 eq) in dioxane (1.8 mL), 3-fluoro-4-(methylsulfonyl)phenylboronic acid (0.047 g, 0.217 mmol, 2.5 eq), Pd(Ph3P)2Cl2 (0.006 g, 0.0087 mmol, 0.1 eq), potassium carbonate (0.06 g, 0.435 mmol, 5 eq) and water (0.8 mL) were added. The reaction mixture was subjected to MW irradiation (120° C., 35 min, 200 W), cooled to RT and concentrated. The residue was purified by silica gel chromatography (0-0.5% MeOH in DCM). Product fractions afforded an oily residue that was further purified by trituration with Et2O providing a pale yellow solid (0.02 g) and by preparative HPLC to give the pure product (0.010 g, 25%). HPLC-MS: (50-100% B in 8 min, 0.6 mL/min): tR=2.41 min, [M+H]+ m/z 448.1. 1H NMR (300 MHz, CDCl3) δ/ppm 8.03 (dd, J=8.3, 7.7, 1H), 7.81-7.70 (m, 2H), 7.39 (dt, J=3.4, 2.0, 2H), 6.94 (d, J=8.2, 1H), 3.96 (s, 3H), 3.94 (s, 3H), 3.26 (s, 3H), 2.59 (s, 3H).

Provenance & Evidence