Sodium hydride → 2-(4-morpholinyl)ethyl 9-(3,5-dinitrobenzyl)-4-(methoxymethyl)-9H-beta-carboline-3-carboxylate

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Reaction Steps

The title compound was prepared according to Method A, using 2-(4-morpholinyl)ethyl 4-(methoxymethyl)-9H-β-carboline-3-carboxylate (100 mg, 0.27 mmol), sodium hydride (0.30 mmol, 12 mg of 60% mineral oil suspension), and 3,5-dinitrobenzyl chloride (65 mg, 0.30 mmol) in DMF (2 mL). Purification of the crude material by preparative thin layer chromatography with ethyl acetate/hexane (7:3) afforded 2-(4-morpholinyl)ethyl 9-(3,5-dinitrobenzyl)-4-(methoxymethyl)-9H-β-carboline-3-carboxylate (107 mg, 72%). 1H NMR (CDCl3) δ8.98 (s, 1H), 8.81 (s, 1H), 8.44 (d, J=8.0 Hz, 1H), 8.31 (d,J=1.9 Hz, 2H), 7.68 (t,J=7.3 Hz, 1H), 7.49 (t,J=7.6 Hz, 1H), 7.42 (d, J=8.3 Hz, 2H), 5.83 (s, 2H), 5.44 (s, 2H), 4.59 (t,J=5.8 Hz, 2H), 3.76 (t, J=4.5Hz, 4H), 3.56 (s, 3H), 2.85 (t,J=5.8Hz, 2H), 2.63 (t,J=4.5 Hz, 4H); MS (APCI; (M+H)+) m/z 550.

Provenance & Evidence