3-Pyridinepropanol → 3-(3-Pyridyl)propyl 9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylate

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Reaction Steps

A suspension of 3-(1-imidazolylcarbonyl)-9-(2,5-dichlorobenzyl)-9H-β-carboline (505 mg, 1.20 mmol) and 3-pyridinepropanol (8.2 g, 60 mmol) was heated at 80° C. in toluene (15 mL) for 22 hours. The resulting solution was cooled to room temperature, and extracted several times with water before drying the organic phase with Na2SO4. Evaporation of the solvent followed by preparative thin layer chromatography of the resulting crude material with hexane/ethyl acetate (6:4) as eluent furnished the desired product (470 mg, 80% yield) as a pale yellow solid. 1H NMR (CDCl3) δ8.91 (s, 1H), 8.88 (s, 1H), 8.56 (s, 1H), 8.48 (s, 1H), 8.31 (d,J=8.0 Hz, 1H), 7.67 (AB q, J=7.4 Hz, 1H), 7.60 (d, J=7.8 Hz, 1H), 7.42-7.48 (m, 3H), 7.22-7.28 (m, 2H), 6.60 (s, 1H), 5.70 (s, 2H), 4.53 (t,J=6.5 Hz, 3H), 2.87 (t, J=7.7 Hz, 3H), 2.26 (t, J=7.3 Hz, 3H); MS (ACPl; (M+H)+) m/z 490.

Provenance & Evidence