Sodium Carbonate → Ethyl 5-(trifluoromethyl)-1-(6-{2-[(4-{(E)-2-[4-(trifluoromethyl)phenyl]vinyl}benzyl)oxy]phenyl}pyridin-2-yl)-1H-pyrazole-4-carboxylate

Beteiligte Stoffe

Reaktionsschritte

To a vial containing the title compound from Example 2 Step A (50.0 mg, 0.092 mmol) were added 2-(4-trifluoromethylphenyl)vinyl boronic acid (29.6 mg, 0.137 mmol) and trans-dichlorobis(triphenylphosphine) palladium (II) (6.4 mg, 0.009 mmol). Acetonitrile (0.400 mL) and sodium carbonate (0.229 mL, 1.0 M aqueous, 0.229 mmol) were added, and the resulting mixture was degassed via nitrogen sparge. The reaction vial was capped and placed in a pre-heated oil bath (70° C.). After 18 h, the reaction mixture was allowed to cool to ambient temperature and was poured into water. The mixture was extracted with DCM, and the organic phase was concentrated in vacuo. Purification by chromatography on silica gel (0 to 30% EtOAc in hexanes, then 30 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 638.4 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.16 (d, J=8.0 Hz, 1H), 8.13 (s, 1H), 7.97 (d, J=7.5 Hz, 1H), 7.88 (t, J=7.5 Hz, 1H), 7.61 (br s, 4H), 7.54 (d, J=8.0 Hz, 1H), 7.52 (d, J=8.5 Hz, 2H), 7.41-7.39 (m, 1H), 7.37 (d, J=7.5 Hz, 1H), 7.21-7.06 (m, 4H), 5.18 (s, 2H), 4.38 (q, J=7.0 Hz, 2H), 1.39 (t, J=7.0 Hz, 3H).

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