Potassium Carbonate → 1-(2-{[4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-yl]oxy}pyridin-3-yl)ethanone

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Reaction Steps

4-Bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol (1-6) (1 g, 3.52 mmol, 1.0 equiv.), 3-acetyl-2-fluoropyridine (0.979 g, 7.04 mmol, 2.0 equiv.) and potassium carbonate (0.973 g, 7.04 mmol, 2.0 equiv.) were dissolved in acetonitrile (10 ml). The mixture was irradiated at 200° C. in microwave reactor until LCMS showed mostly desired product. The solvent was evaporated in vacuo, the mixture was neutralized with saturated aqueous NH4Cl, and then extracted with EtOAc. The organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (EtOAc/Hexane gradient from 0 to 100%) to obtain 2. 1H NMR (CDCl3) δ 8.30-8.24 (1H, m), 8.24 (1H, s), 7.83 (1H, d, J=2.06 Hz), 7.56 (1H, d, J=8.91 Hz), 7.29 (1H, dd, J=2.1, 8.9 Hz), 7.16-7.10 (1H, m), 4.42 (2H, s), 2.80 (3H, s), 1.09 (9H, s) ppm. LRMS m/z (M+H) 403.0 and 405.0 (intensity ratio ˜1:1) found, 403.1 and 405.1 required.

Provenance & Evidence