Ethylamine → HCID 86631947, compound

Participants

Reaction Conditions

Reaction Steps

1-tert-Butyl 4-methyl 3-iodo-2,5-dimethylterephthalate (300 mg, 0.769 mmol) was dissolved in dioxane (3 mL) and sparged with nitrogen for 15 minutes. XANTPHOS (18 mg, 0.031 mmol), cesium carbonate (326 mg, 1.00 mmol), ethylamine (0.1 mL) and tris(dibenzylideneacetone)dipalladium (14 mg, 0.015 mmol) were added, and the mixture was stirred in a sealed tube at 95° C. for 19 h. XANTPHOS (36 mg, 0.062 mmol), ethylamine (0.1 mL) and tris(dibenzylideneacetone)dipalladium (28 mg, 0.030 mmol) were added and the mixture was stirred in a sealed tube at 95° C. for a further 20 h. The reaction mixture was cooled to ambient temperature and was filtered through celite. The filter cake was washed with ethyl acetate, and the filtrate was concentrated to afford an orange oil which was purified by column chromatography (silica gel, 2-10% ethyl acetate in hexanes) to afford 1-tert-butyl 4-methyl 3-(ethylamino)-2,5-dimethylterephthalate (158 mg, 0.515 mmol, 67% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.08 (s, 1H), 3.91 (s, 3H), 3.83 (br s, 1H), 3.00 (q, 2H), 2.36 (s, 3H), 2.29 (s, 3H), 1.59 (s, 9H), 1.14 (t, 3H); MS (EI) for C17H25NO4: 308 (MH+).

Provenance & Evidence