Methanol → 7-(2-{1-[1-(3-Benzyloxy-phenyl)-2-ethoxycarbonyl-ethyl]-1H-indol-5-yloxy}-ethyl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

Samarium (II) iodide [0.1 M in THF] (14.8 mL, 14.8 mmol) was added to a solution of 7-(2-{1-[1-(3-benzyloxy-phenyl)-2-ethoxycarbonyl-vinyl]-1H-indol-5-yloxy}-ethyl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (0.10 g, 0.15 mmol), hexamethylphosphoramide (0.39 mL, 2.22 mmol) and either ethanol or methanol (10 equivalents) and stirred at room temperature overnight. Saturated ammonium chloride (20 mL) was added to the reaction and the crude product was extracted with ethyl acetate (3×20 mL). The crude mixture was then purified via column chromatography in silica gel (20% ethyl acetate in hexane) to give the title compound (0.50 g, 50% yield). 1H NMR (CDCl3) δ 7.28–7.22 (m, 5H), 7.13 (m, 4H), 7.08 (d, 1H, J=3.2 Hz), 6.86 (m, 1H), 6.79–6.69 (m, 4H), 6.35 (d, 1H, J=3.2 Hz), 5.99 (t, 1H, J=7.5 Hz), 4.98 (s, 2H), 4.29 (t, 2H, J=6.9 Hz), 3.96 (q, 2H, J=7.1 Hz), 3.68 (m, 2H), 3.18–3.10 (m, 4H), 2.66 (m, 2H), 1.85 (m, 2H), 1.45 (s, 9H), 1.01 (t, 3H, J=7.1 Hz).

Provenance & Evidence