Trimethylsilyl iodide → Ethyl 1-[6-(2-hydroxy-5-methylphenyl)-4-iodopyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

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Reaction Steps

A solution of the title compound from Example 19 Step F (1 g, 1.88 mmol) and iodotrimethylsilane (3.6 mL) in 15 mL chloroform was heated at 80° C. for 7 h. A second portion of iodotrimethylsilane (2 mL) was added and heating was continued at 90° C. overnight. The volatiles were removed in vacuo. Toluene was added, and the volatiles were removed in vacuo. Finally, dry MeOH was added, and the volatiles were removed in vacuo. Silica gel flash chromatography using hexanes:EtOAc (20:1 to pure EtOAc) gave the title compound: LCMS m/z 518.6 [M+H]+; 1H NMR (400 MHz, acetone-d6) δ 8.87 (d, J=1.1 Hz, 1H), 8.24 (s, 1H), 8.12 (d, J=1.1 Hz, 1H), 7.89 (d, J=2 Hz, 1H), 7.18 (dd, J=8.5, 2.0 Hz, 1H), 6.84 (d, J=8.3 Hz, 1H), 4.37 (q, J=7.1 Hz, 2H), 2.30 (s, 3H), 1.35 (t, J=7.1 Hz, 3H).

Provenance & Evidence