Potassium Carbonate → 2-(3,4-Dimethoxyphenyl)-6-methylimidazo[2,1-b][1,3,4]thiadiazole

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Reaction Conditions

Reaction Steps

To a mixture of 2-bromo-6-methyl-imidazo[2,1-b][1,3,4]thiadiazole (0.550 g, 2.522 mmol, 1 eq), 3,4-dimethoxyphenylboronic acid (0.551 g, 3.026 mmol, 1.2 eq) and Pd(dppf)Cl2.DCM (0.209 g. 0.252 mmol, 0.1 eq) in DME (3 mL) was added K2CO3 (1 mL, sat. aq). The mixture was heated in the microwave oven (130° C., 1 h), cooled to RT, diluted with DCM, washed with water, dried (Na2SO4) and concentrated. The residue (yellow solid, 0.720 g) was purified by automated flash chromatography (SiO2, DCM/0-40% MeOH) to give the desired product (yellow solid, 0.347 g, 50%). HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=3.77 min, [M+H]+ m/z 276.1.

Provenance & Evidence