Dichloromethane → 5-[2-(3,4-Dimethoxy-phenyl)-6-methyl-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-3-trifluoromethyl-pyridin-2-ylamine

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Reaction Steps

A mixture of 2-(3,4-dimethoxy-phenyl)-5-iodo-6-methyl-imidazo[2,1-b][1,3,4]thiadiazole (0.125 g, 0.312 mmol, 1 eq), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (0.119 g, 0.414 mmol, 1.33 eq), Pd(dppf)Cl2.DCM (0.008 g, 0.009 mmol, 0.03 eq) and cesium carbonate (0.305 g, 0.935 mmol, 3 eq) in DME (4 mL) and water (0.1 mL) was heated in the microwave oven (45 min, 130° C.), cooled to RT, diluted with water, extracted with EtOAc and washed with brine. The organic layers were dried (MgSO4), filtered and concentrated, and the residue was purified by silica gel chromatography (0-100% EtOAc in hexane). Product fractions were concentrated and triturated with Et2O, the solid was filtered off and dried to give the desired product (solid, 0.070 g, 52%). HPLC-MS: (50-100% B in 8 min, 0.8 mL/min): tR=1.11 min, [M+H]+ m/z 436.0. 1H NMR (300 MHz, CDCl3) δ/ppm 8.62 (d, J=1.6, 1H), 8.22 (d, J=1.6, 0H), 7.44 (d, J=2.2, 1H), 7.39 (dd, J=8.2, 2.2, 1H), 6.96 (d, J=8.5, 1H), 5.11 (s, 1H), 3.99 (s, 3H), 3.97 (s, 3H), 2.53 (s, 1H).

Provenance & Evidence