Triphenylphosphine → 2-[1-(2-fluorobenzenesulfonyl)-1H-indol-4-yloxy]ethyl methylcarbamic acid tert-butyl ester

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A 100 mL flask equipped with a magnetic stirrer and a rubber septum was charged with triphenyl phosphine (0.506 g, 0.0019 mol) and 1-(2-fluorobenzenesulfonyl)-4-hydroxy-1H-indole (0.330 g, 0.0012 mol), and purged with N2. The mixture was cooled to 0° C. and freshly distilled THF was added (45 mL). A solution of 2-hydroxyethyl methylcarbamic acid tert-butyl ester (0.317 g, 0.0018 mol) and diethylazodicarboxylate (0.337 g, 0.0019 mol) in 5 mL of THF was added dropwise at 0° C. to give a yellow solution. The reaction mixture was warmed to ambient temperature and stirred for 72 hours, concentrated in vacuo and the resulting crude oil was purified by flash chromatography using a 25:75 of hexanes/ethyl acetate mixture to give 2-[1-(2-fluorobenzenesulfonyl)-1H-indol-4-yloxy]ethyl methylcarbamic acid tert-butyl ester as a clear oil (0.483 mg; 89%). 1H NMR (300 MHz, CDCl3) δ: 1.44 (bs, 9 H), 3.01 (s, 3 H), 3.65 (bs, 2 H), 4.19 (bs, 2 H), 6.65 (d, 1 H, J=8.03), 6.76 (d, 1 H, J=3.77), 7.09 (t, 1 H, J=8.67). 7.17 (t, 1 H, J=8.11), 7.28 (t, 1 H, J=7.73), 7.44 (d, 1 H, J=8.29), 7.55 (m, 2 H), 803 (t, 1 H, J=7.44).

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