(E)-5-(2-(phenylsulfonyl)vinyl)-1H-indole → 3-Dealkyl eletriptan

Participants

Reaction Steps

A suspension of (E)-5-(2-(phenylsulfonyl)vinyl)-1H-indole (5.0 g) in 50 ml methanol, 10 ml THF and 10% Pd/C (1.0 g) was subject to hydrogenation at 45-50 psi. Upon completion of the reaction the catalyst was filtered off and the solvent removed under vacuum to provide the title compound in about 85-90% yield as an off-white solid. 1H NMR CDCl3 δ=8.15 (bs, NH), 7.93-8.00 (m, 2H), 7.53-7.70 (m, 3H), 7.38 (s, 1H), 7.30 (d, 1H), 7.20 (dd, 1H), 6.93 (dd, 1H), 6.42-6.48 (m, 1H), 3.37-3.46 (m, 2H), 2.99-3.17 (m, 2H). ESI Mass (M+23) 308.4

Provenance & Evidence