Reaction Steps
Ethyl 1-(cyanomethyl)-6-iodoindole-2-carboxylate (1.77 g, 5 mmol) was added portion-wise over 2 min to a stirred suspension of lithium aluminium hydride (0.48 g, 13 mmol) in ether (50 mL) at 0° C. under Ar. The reaction was then heated to reflux and stirred for 18 h. After allowing to cool to room temperature the mixture was poured into a mixture of saturated aqueous potassium sodium tartrate solution (150 mL) and ethyl acetate (100 mL). The mixture was filtered through celite and the biphasic filtrate was separated. The aqueous layer was extracted with ethyl acetate (2×50 mL) and the combined organic extracts were washed with brine (1×75 mL), dried (magnesium sulfate), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by flash column chromatography [SiO2; ethyl acetate-methanol, (9:1)] to give the product as a yellow solid (0.47 g, 32%, contains 15% of de-iodinated material). IR νmax (Nujol)/cm−1 3306, 2924, 2855, 1882, 1735, 1664, 1598, 1527, 1460, 1410, 1378, 1356, 1338, 1322, 1298, 1282, 1246, 1218, 1202, 1170, 1143, 1116, 1045, 1001, 984, 943, 919, 876, 840, 814, 773, 740, 698, 637, 617, 589, 522 and 488; NMR δH (400 MHz; CDCl3) 7.60 (1H, m), 7.35–7.37 (1H, m), 7.28 (1H, d, J 7.8 Hz), 6.15 (1H, m), 4.19 (2H, m), 3.94 (2H, t, J 5.8 Hz), 3.33 (2H, t, J 5.8 Hz), 1.79 (1H, br. s).
