Fumaric Acid → 5-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]-1H-indole Fumarate

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Reaction Steps

The product of Example 3A (80 mg, 0.25 mmol) was treated with fumaric acid (29 mg, 0.25 mmol) in EtOAc/EtOH (v. 1:1, 4 mL) at ambient temperature for 10 h. The title compound was obtained as solid (57 mg, yield, 52%). 1H NMR (300 MHz, CD3OD) δ 1.78–2.16 (m, 3H), 2.25–2.39 (m, 1H), 2.46–2.54 (m, 1H), 3.14–3.45 (m, 5H), 3.69–3.81 (m, 1H), 4.80–4.89 (m, 1H), 6.46 (dd, J=3.0, 1.0, 1H), 6.68 (s, 2H), 7.02 (dt, J=8.8, 2.5 Hz, 2H), 7.23 (d, J=3.1 Hz, 1H), 7.31 (dd, J=8.5, 2.0 Hz, 1H), 7.43 (dt, J=8.4, 0.8 Hz, 1H), 7.58 (dt, J=9.2, 2.6 Hz, 2H), 7.71 (dd, J=1.7, 1.0 Hz, 1H) ppm. MS (DCl/NH3): m/z 319 (M+H)+. Anal. Calculated for C21H22N2O.C4H4O4: C, 69.11; H, 6.03; N, 6.45. Found: C, 69.23; H, 5.81; N, 6.59.

Provenance & Evidence