HCID 86686447, compound → HCID 86686448, compound

Participants

Reaction Steps

5-(Benzyloxy)-1-(pentan-2-yl)-1H-indole (8) (3.80 g, 12.9 mmol) was dissolved in methanol (MeOH, 30.0 mL) and 10% palladium on activated charcoal (Pd/C, 1.37 g, 0.129 mmol, 10 mol % Pd) was added. The mixture was placed under an atmosphere of hydrogen (double balloon), stirred overnight at room temperature, and then filtered over Celite® (MeOH eluent, 500 mL). Evaporation of the solvent under reduced pressure afforded 1-(pentan-2-yl)-1H-indol-5-ol (9) (2.60 g, 100%) as an oil. 1H NMR (500 MHz, CDCl3): δ 7.25 (d, J=9.0, 1H), 7.18 (d, J=3.0 Hz, 1H), 7.05 (d, J=2.0 Hz, 1H), 6.80 (dd, J=9.0, 2.0, 1H), 6.41 (d, J=3.0 Hz, 1H), 4.56 (bs, 1H), 4.43 (m, 1H), 1.87 (m, 2H), 1.52 (d, J=6.5, 3H), 1.26 (m, 2H), 0.90 (t, J=7.5, 3H).

Provenance & Evidence