Sodium hydride → methyl 9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylate

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Reaction Steps

To a suspension of sodium hydride (1.60 g of 60% dispersion in oil, 0.04 mol) in dry DMF (60 mL) was added methyl 9H-β-carboline-3-carboxylate (8.7 g, 0.0385 mol) at −20° C. with stirring. The mixture was allowed to warm to room temperature with stirring under nitrogen. After stirring for 10 minutes at room temperature, formation of the sodium salt of the β-carboline appeared to be complete, resulting in a clear brown solution. The reaction mixture was cooled in an ice bath, 2,5-dichlorobenzyl chloride (7.82 g, 0.040 mol) was added, and the mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with water (200 mL), filtered, and the cake washed with water, ethyl acetate, ether, and dried, affording 13.05 g (88%) of the title product. 1H NMR (CDCl3) δ8.88 (s, 1H), 8.78 (s, 1H), 8.20 (d, J=7.8 Hz, 1H), 7.61 (t, J=7.8 Hz, 1H), 7.45-7.35 (m, 3H) 7.18 (dd, J=8.2, 1.7 Hz,1H), 6.52 (s, 1H), 5.56 (s, 2H), 4.06 (s, 3H); MS (APCI; (M+H)+) m/z 385.

Provenance & Evidence