2-(1-Azidoethyl)-3-phenyl-1-(toluene-4-sulfonyl)-1H-indole → 1-[3-phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]ethylamine

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Reaction Steps

A mixture of 2-(1-azidoethyl)-3-phenyl-1-(toluene-4-sulfonyl)-1H-indole (1.34 g, 3.22 mmol) and 10% Pd/C (200 mg) in EtOAc (80 mL) was degassed with a stream of nitrogen and stirred at RT under a hydrogen atmosphere for 20 h. The suspension was then filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) affording 1-[3-Phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]ethylamine as a white solid (960 mg, 76%). 1H NMR (CDCl3, 400 MHz): δ 8.18 (1H, d, J=8.44 Hz), 7.73 (2H, d, J=8.44 Hz), 7.49-7.15 (10H, m), 4.72 (1H, q, J=6.96 Hz), 2.35 (3H, s), 1.45 (3H, d, J=7.40 Hz)

Provenance & Evidence