反应详情

To a solution of 4-(carboethoxymethyl)indole (830 mg, 4.12 mmol) and ethyl bromopyruvate 2-oxime (866 mg, 4.12 mmol) in methylene chloride (40 mL) was added anhydrous Na2CO3 (2.40 g, 22.66 mmol) at room temperature. After stirring at room temperature for 16 hours, the mixture was filtered and concentrated to dryness. The residue was flash chromatographed on silica gel (eluting (10% MeOH/CHCl3):hexane=1:1→2:1) to give 0.98 g of the title compound; TLC Rf =0.61 (10% MeOH/CHCl3). MS(CI) m/e 333 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ8.17 (br s, --NH), 8.03 (br s, --OH), 7.26 (d, J=7.4 Hz, 1H), 7.12 (t, J=7.4 Hz, 1H), 6.98 (d, J=7.4 Hz, 1H) 6.92 (br s, 1H), 4.30 (s, 2 H), 4.28 (q, J=7.4 Hz, 2H), 4.18 (q, J=7.4 Hz, 2H), 4.13 (s, 2H), 1.30 (t, J=7.4 Hz, 3H), 1.25 (t, J=7.4 Hz, 3H).

1. filtrationthe mixture was filtered
2. concentrationconcentrated to dryness
3. customchromatographed on silica gel (eluting (10% MeOH/CHCl3):hexane=1:1→2:1)