Ethylenediamine → 2,5-Dichloro-1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-3-methanesulfonyl-1H-indole

Participants

Reaction Steps

To a solution of ethylene diamine(0.065 g, 1.092 mmole) in ethanol:chloroform (30 ml, 1:1) at 0° C. under a nitrogen atmosphere was added 2-(2,5-dichloro-3-methanesulfonyl-indol-1-yl)-acetimidic acid ethyl ester hydrochloride (0.351 g, 0.91 mmole) dissolved in chloroform (5 ml). The reaction mixture was stirred at room temperature for 2 h and then evaporated to dryness. The residue was purified by column chromatography (silica gel) eluting the product with 7:93 methanol:methylene chloride with 0.1% ammonium hydroxide added. The resulting product, pure 2,5-dichloro-1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-3-methanesulfonyl-1H-indole weighed 0.314 g (99.7% yield).

Provenance & Evidence