Cesium carbonate → 4-[(3,3-Dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester

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Reaction Steps

Following general procedure E and using 5-amino-3,3-dimethyl-7-isopropyl-2,3-dihydrobenzofuran (Compound 13, 0.085 g, 0.5 mmol), ethyl-4-iodo-benzoate (0.123 g, 0.5 mmol), cesium carbonate (0.228 g, 0.7 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.020 g, 0.021 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.040 g, 0.064 mmol) in 2 mL of anhydrous toluene (reacted in a sealed tube), the title compound (0.107 g, 76%) was obtained. 1H NMR (300 MHz, CDCl3): δ 7.89(d, 2H, J=8.8 Hz), 6.85 (d, 1H, J=2.0 Hz), 6.80 (d, 1H, J=2.0 Hz), 6.78 (d, 2H, J=8.8 Hz), 5.84 (br s, 1H), 4.32 (q, 2H, J=7.2 Hz), 4.25 (s, 2H), 3.08 (heptet, 1H, J=6.9 Hz), 1.36 (t, 3H, J=7.2 Hz), 1.33 (s, 6H), 1.23 (d, 6H, J=6.9 Hz).

Provenance & Evidence