5-nitro-1-(2-pyrrolidin-1-ylethyl)-1H-indole → 5-Amino-1-(2-pyrrolidin-1-ylethyl)indole

Participants

Reaction Steps

Dissolve 5-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indole (375 mg, 1.45 mmol) in ethanol (15 mL) and add 5% Pd/C (149 mg). Purge the black mixture with hydrogen (1 atm) and stir overnight under a hydrogen atmosphere. Filter the black mixture through Celite® and wash the solids with additional ethanol (˜10 mL). Concentrate the filtrate to give the title compound as a yellow solid. MS (ES+) 230.2 (M+1)+. 1H NMR (400 MHz, CDCl3): δ: 7.17 (d, 1H, J=8.8 Hz), 7.05 (d, 1H, J=3.1 Hz), 6.92 (d, 1H, J=2.2 Hz), 6.67 (dd, 1H, J=8.3, 2.2 Hz), 6.29 (d, 1H, J=3.1 Hz), 4.21 (t, 2H, J=7.5 Hz), 3.37 (s, 2H), 2.86 (t, 2H, J=7.5 Hz), 2.55 (m, 4H), 1.79 (m, 4H).

Provenance & Evidence