Diisopropylamine → HCID 68881428, compound

Participants

Reaction Steps

5-Chloro-7-iodo-1,3-benzodioxol-5-amine (682 mg, 2.29 mmol) and N,N-dimethyl-N′-prop-2-yn-1-ylurea (289 mg, 2.29 mmol) in ethyl acetate (10 ml) were cooled in ice-methanol, under an atmosphere of nitrogen, then treated with bis(triphenylphosphine) palladium(II) dichloride (161 mg, 10 mol %) followed by copper(I) iodide (43 mg, 10 mol %) and diisopropylamine (463 mg, 4.03 mmol). The reaction was allowed to warm to room temperature and stirred 3 hr. 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]-N,N-dimethylurea (463 mg, 68%) as an off-white solid; NMR Spectrum:(DMSOd6) 2.79 (s, 6H), 4.01 (d, 2H), 5.50 (s, 2H), 6.05 (s, 2H), 6.78 (t, 1H), 6.79 (s, 1H).

Provenance & Evidence