Diisopropylamine → N-[3-(7-amino-6-chloro-1,3-benzodioxol-4-yl)prop-2-yn-1-yl]morpholine-4-carboxamide

Participants

Reaction Steps

5-Chloro-7-iodo-1,3-benzodioxol-4-amine (600 mg, 2.02 mmol) and N-prop-2-yn-1-ylmorpholine-4-carboxamide (406 mg, 2.42 mmol) in ethyl acetate (10 ml) were cooled in ice-methanol, under an atmosphere of nitrogen, and then treated with bis(triphenylphosphine) palladium(II) dichloride (140 mg, 10 mol %) followed by copper(I) iodide (38 mg, 10 mol %) and diisopropylamine (407 mg, 4.03 mmol). The reaction was allowed to warm to room temperature and stirred for 3 hours and then filtered through Celite. The filtrate was purified by column chromatography on silica using ethyl acetate as eluent to give N-[3-(7-amino-6-chloro-1,3-benzodioxol-4-yl)prop-2-yn-1-yl]morpholine-4-carboxamide (529 mg, 78%) as a pale brown solid; NMR Spectrum:(DMSOd6) 3.28 (m, 4H), 3.54 (m, 4H), 4.05 (d, 2H), 5.47 (s, 2H), 6.05 (s, 2H), 6.78 (s, 1H), 7.01 (t, 1H); Mass Spectrum: M+H+ 338/340.

Provenance & Evidence