4-(benzyloxy)-1-ethyl-6-fluoro-3-(2-(isoindolin-2-yl)ethyl)-1H-indole → 1-ethyl-6-fluoro-3-(2-(isoindolin-2-yl)ethyl)-1H-indol-4-ol

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Reaction Steps

To a solution of 31-3 (30 mg, 0.072 mmol) in methanol (10 mL) was added 10% Pd/C (20 mg) under hydrogen atmosphere. The reaction mixture was stirred at room temperature overnight and then filtered through a pad of celite. The filtrate was concentrated to give a pale yellow residue, which was purified on silica gel column chromatography eluting with dichloromethane/methanol (9:1) to give 31-4 (25 mg, 70%) as a white solid. 1H-NMR (400 MHz, CDCl3): δ (ppm) 7.29 (d, J=2.4 Hz, 2H), 7.17 (d, J=3.2 Hz, 2H), 6.76 (s, 1H), 6.50 (d, J=8.8 Hz, 1H), 6.30 (d, J=10.8 Hz, 1H), 5.00-4.96 (br.s, 2H), 4.34-4.32 (br.s, 2H), 3.96 (q, 2H), 3.59-3.57 (br.s, 2H), 3.32-3.30 (br.s, 2H), 1.37 (t, J=7.6 Hz, 3H). LRMS: calc 324.2 and found: 325.1 [M+1].

Provenance & Evidence