Cesium carbonate → 4-[Isopropyl-(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 3,3-dimethyl-7-isopropyl-5-(isopropyl)amino-2,3-dihydro-benzofuran (Compound 35, 0.21 g, 0.86 mmol), ethyl-4-iodo-benzoate (0.0.29 g, 1.03 mmol), cesium carbonate (0.39 g, 1.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.020 g, 0.020 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.04 g, 0.064 mmol) in 6 mL of anhydrous toluene, the title compound (0.027 g) was obtained; some of the product was eluted as a mixture with the starting amine. Some 5-(isopropyl)amino-3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran (Compound 35) was also recovered. 1H NMR (300 MHz, CDCl3): δ 7.82 (d, 2H, J=9.2 Hz), 6.72 (d, 1H, J=2.0 Hz), 6.64 (d, 1H, J=2.0 Hz), 6.50 (d, 2H, J=9.0 Hz), 4.40-4.26 (m, 5H), 3.10 (heptet, 1H, J=7.0 Hz), 1.34 (t, 3H, J=7.1 Hz), 1.33 (s, 6H), 1.23 (d, 6H, J=7.0 Hz), 1.15 (d, 6H, J=6.5 Hz).

Provenance & Evidence