HCID 86686447, compound → HCID 86686448, compound

Participants

Reaction Steps

5-(Benzyloxy)-1-(pentan-2-yl)-1H-indole (8) (10.67 g, 36.4 mmol, 1.0 equiv.) was dissolved in MeOH (90 mL), and 10% wt. Pd/C was added (3.87 g, 3.64 mmol, 0.10 equiv). The reaction mixture was placed under a hydrogen atmosphere using double balloons, and stirred for 24 h at room temperature. The mixture was filtered through a Celite® pad and washed with (800 mL). The filtrate was concentrated to afford 1-(pentan-2-yl)-1H-indol-5-ol (9) as a brown oil, which was used without any further purification in the next step. 1H NMR (500 MHz, CDCl3) δ7.23 (d, J=8.8 Hz, 1H), 7.15 (d, J=2.9 Hz, 1H), 7.03 (d, J=1.8 Hz, 1H), 6.77 (dd, J=8.7, 2.0 Hz, 1H), 6.39 (d, J=2.8 Hz, 1H), 4.52 (br, 1H), 4.42 (m, 1H), 1.87 (m, 1H), 1.76 (m, 1H), 1.49 (d, J=6.8 Hz, 3H), 1.23 (m, 2H), 0.88 (t, J=7.4 Hz, 3H).

Provenance & Evidence