Cesium carbonate → (2S)-3-(4-{3-[4-(1H-Indol-5-yl)-phenoxy]-propoxy}-phenyl)-2-methoxy-propionic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of (2S)-3-{4-[3-(4-iodo-phenoxy)-propoxy]-phenyl}-2-methoxy-propionic acid ethyl ester (0.10 mmol, 50 mg) (Step A), 5-indolyl-boronic acid (0.114 mmol, 18 mg) and powered cesium carbonate (0.23 mmol, 35 mg) in DME (0.5 mL) was added Pd(PPh3)4 (0.003 mmol, 4 mg). The mixture was flushed with nitrogen and maintained under nitrogen while being heated at reflux in a 100° C. oil bath. The mixture was stirred for 6 hours, and then cooled to room temperature and diluted with ethyl acetate and water. The organic layer was dried (Na2SO4) and concentrated. The crude product was purified by chromatography on silica gel (CH2Cl2/EtOAc 96:4) to afford the title compound 1H-NMR (CDCl3, 200.15 MHz): δ 8.20 (broad s, 1H), 7.80 (d, 1H, J=0.8), 7.56 (d, 3H, J=8.9), 7.41 (d, 2H, J=1.6), 7.23 (dd, 1H, J=3.2, 2.4), 7.15 (d, 3H, J=8.6), 6.99 (d, 2H, J=8.9), 6.85 (d, 3H, J=8.6), 6.60–6.58 (m, 1H), 4.24–4.11 (m, 8H), 3.92 (dd, 1H, J=7.3, 5.9), 3.35 (s, 4H), 2.98–2.94 (m, 3H), 2.28 (qn, 2H, J=5.9), 1.24 (t, 4H, J=7.3).

Provenance & Evidence