Cesium carbonate → Ethyl 1-(6-(2-((4-bromobenzyl)oxy)-5-methylphenyl)pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a vial containing the title compound from Example 12 Step B (320 mg, 0.82 mmol) were added 4-bromobenzyl bromide (245 mg, 0.98 mmol), cesium carbonate (533 mg, 1.64 mmol), and DMF (3 mL), and the resulting mixture was stirred at 45° C. After 1 h, the reaction mixture was allowed to cool to ambient temperature, then was loaded directly onto a silica gel column and purified (0 to 30% EtOAc in hexanes, then 30% EtOAc in hexanes) to provide the title compound: LCMS m/z 562.4 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.13 (s, 1H), 8.08 (d, J=8.0 Hz, 1H), 7.87 (t, J=8.0 Hz, 1H), 7.77 (d, J=3.0 Hz, 1H), 7.53 (d, J=8.0 Hz, 1H), 7.47 (d, J=8.5 Hz, 2H), 7.22 (d, J=8.5 Hz, 2H), 7.16 (dd, J=8.0, 3.0 Hz, 1H), 6.92 (d, J=8.5 Hz, 1H), 5.06 (s, 2H), 4.39 (q, J=7.0 Hz, 2H), 2.35 (s, 3H), 1.40 (t, J=7.0 Hz, 3H).

Provenance & Evidence