Trifluoroacetic acid → 2-(1-ethyl-4-methoxy-6-phenyl-1H-indol-3-yl)-N,N-dimethylethanamine

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Reaction Steps

36-5 (68 mg, 0.2 mmol) was dissolved in DCM (2 mL) and triethylsilane (0.32 mL, 2.0 mmol) was added at 0° C. Trifluoroacetic acid (126 uL, 1.6 mmol) was added dropwise. After 20 minutes, the reaction mixture was quenched with saturated aqueous sodium bicarbonate and then diluted with DCM. The organic layer was dried over MgSO4, filtered, and evaporated. The resulting residue was purified on silica gel column chromatography eluting with DCM/methanol (0-10%) containing 0.1% NH4OH to give the desired product. The product was acidified with HCl to afford 36-6 (19.6 mg, 27%) as an off-white solid. 1H NMR (300 MHz, D2O): δ (ppm) 7.62 (m, 2H), 7.42-7.24 (m, 4H), 7.06 (s, 1H), 6.78 (s, 1H), 4.04 (q, J=7.5 Hz, 2H), 3.88 (s, 3H), 3.31 (t, J=8.4 Hz, 2H), 3.12 (t, J=7.5 Hz, 2H), 2.76 (s, 6H), 1.24 (s, 7.5 Hz, 3H). LCMS: calc 322.4 and found: 323.1 [MH]+.

Provenance & Evidence