Potassium Fluoride → HCID 44193859, compound

Participants

Reaction Steps

In a microwave vial a mixture of (4-bromo-3-methoxy-phenyl)-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine (120 mg, 0.289 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (185 mg, 0.88 mmol), palladium (II) acetate (6 mg 0.027 mmol) and potassium fluoride (51 mg, 0.867 mmol) in 6 ml methanol was purged with nitrogen. The vial was sealed and the mixture was irradiated for ½ h at 140° C. in a microwave oven. The reaction mixture was filtered and the filtrate was concentrated, the residue was dissolved in dichloromethane, washed three times with water, dried and evaporated in vacuo. Column chromatography (12 g silica, dichloromethane+1.8% methanol v/v) afforded the title compound (19 mg, 16%) as a light brown wax. MS ISP (m/e): 417.1 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.79 (s, 1H), 7.75 (s, 1H), 7.38 (d, 1H), 7.22 (m, 6H), 6.97 (s, broad, 1H), 6.65 (dd, 1H), 4.05 (s broad, 1H), 3.92 (s, 3H), 3.68 (s, 3H), 2.75 (m broad, 2H), 2.20 (m broad, 1H), 1.88 (m broad, 3H).

Provenance & Evidence