1,1'-Carbonyldiimidazole → 2-Methyl-1-(6-phenylpyridin-3-yl)propyl 1H-imidazole-1-carboxylate

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Reaction Steps

Synthesized using compound 43a (81 mg, 0.36 mmol), CDI (289 mg, 1.78 mmol) and acetonitrile (5 mL) according to Method E. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (4:1) as eluent. White solid. Yield: 90.0 mg, 90%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=0.95 (d, J=6.9 Hz, 3H), 1.14 (d, J=6.6 Hz, 3H), 2.37 (m, 1H), 5.70 (d, J=8.2 Hz, 1H), 7.09 (dd, J=1.6, 0.6 Hz, 1H), 7.40-7.51 (m, 4H), 7.72-7.79 (m, 2H), 7.98-8.03 (m, 2H), 8.19 (t, J=0.9 Hz, 1H), 8.71 (dd, J=2.2, 0.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=18.7, 18.8, 33.6, 83.7, 117.2, 120.4, 127.1, 129.0, 129.5, 131.1, 131.8, 135.6, 137.2, 138.8, 148.7, 158.0; MS (ESI): m/z=322.32 [M+H]+.

Provenance & Evidence