Potassium Carbonate → 9-[(3-pyridyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one

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A suspension of 5-carbomethoxy-1,2-dihydro-9H-carbazol-4(3H)-one (500 mg, 2.06 mmol), potassium carbonate (860 mg, 18.8 mmol), and catalytic amount of sodium iodide (ca. 10 mg), was treated with 3-picolyl chloride hydrochloride (500 mg, 3.05 mmol). The reaction was stirred at ambient temperature 19.5 hours. The mixture was poured into H2O (100 mL) and the mixture extracted four times with ethyl acetate. The combined organic layers were washed four times with H2O, once with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel (elution with 5% MeOH in EtOAc) to afford 550 mg (80%) of the 9-[(3-pyridyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one as a white solid. 1H NMR (CDCl3) δ8.48 (d, 1H, J=2.9 Hz), 8.43 (br s, 1H), 7.31 (d, 1H, J=7.3 Hz), 7.25-7.09 (m, 5H), 5.29 (s, 2H), 3.97 (s, 3H), 2.80 (t, 2H, J=6.1 Hz), 2.49 (t, 2H, J=6.4 Hz), and 2.20-2.12 (m, 2H). IR (CDCl3, cm−1) 1726, 1656, 1464, 1444, 1434, 1289 and 1119. MS (ES) m/e 335 (M+1).

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