Sodium Carbonate → 2-Methoxy-4-(6-methylimidazo[2,1-b][1,3,4]thiadiazol-2-yl)phenol

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Reaction Steps

To a solution of 2-bromo-6-methyl-imidazo[2,1-b][1,3,4]thiadiazole (1.53 g, 7.02 mmol, 1 eq) in dioxane (30 mL), 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1.76 g, 7.02 mmol, 1 eq) was added followed by 2M aq. Na2CO3 (15 mL, 30 mmol, 4.3 eq). The suspension was degassed (N2, 15 min) and equipped with an argon balloon. Pd(Ph3P)2Cl2 (1.23 g, 1.75 mmol, 0.25 eq) was quickly added, and the reaction flask was placed in a pre-heated bath (115° C.). After stirring at reflux temperature for 2 h the reaction mixture was cooled to RT and concentrated. The residue was taken in water and extracted with DCM; the organic phase was washed with water, dried and concentrated to give 2-methoxy-4-(6-methylimidazo[2,1-b][1,3,4]thiadiazol-2-yl)phenol as a crude product (brown solid, 3 g) that was used in the next step without further purification. HPLC-MS (10-95% B in 4 min +2 min 100% B, flow 0.5 mL/min, 50° C.): tR=3.27 min, [M+H]+ m/z 262.0

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