Aluminum(III) Chloride → 4-(benzyloxy)-1-ethyl-6-fluoro-3-(2-(isoindolin-2-yl)ethyl)-1H-indole

Participants

Reaction Steps

To a solution of LiAlH4 (100 mg, 2.6 mmol) in THF (30 mL) was added aluminum trichloride (463 mg, 3.51 mmol) at 0° C. After stirring for 10 min, a solution of 31-2 (180 mg, 0.42 mmol) in THF (5 mL) was added dropwise. The reaction mixture was stirred for 5 min before Na2SO4.10H2O was added to quench the reaction. The solid was filtered off and the filtrate was evaporated. The resulting residue was purified on silica gel column chromatography eluting with dichloromethane/methanol (10:1) to get 31-3 (100 mg, 57%) as a yellow solid. 1H-NMR (400 MHz, CDCl3): δ (ppm) 7.46 (d, J=7.2 Hz, 2H), 7.31-7.26 (m, 4H), 7.27 (t, J=3.6 Hz, 1H), 7.09-7.06 (m, 2H), 6.93 (s, 1H), 6.65 (d, J=7.2 Hz, 1H), 6.42 (d, J=7.2 Hz, 1H), 5.06 (s, 2H), 4.02-4.00 (m, 6H), 3.27 (s, 4H), 1.41 (t, J=7.4 Hz, 3H). LRMS: calc 414.2 and found: 414.9 [M+1].

Provenance & Evidence