3-Ethynylpyridine → 7-(pyridin-3-ylethynyl)-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

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Reaction Steps

The product of Example 1B (130 mg, 0.45 mmol) and 3-ethynylpyridine (74 mg, 0.72 mmol; Aldrich) were processed according to the method described in Example 3 and purified by reverse-phase HPLC (Waters XBridge™ C18 5 μm OBD 30×100 mm column, flow rate 40 mL/minute, 5-95% gradient of acetonitrile in 0.1% trifluoroacetic acid over 15 minutes) to afford the title compound as the bis trifluoroacetate: 1H NMR (500 MHz, methanol-d4) δ ppm 2.26-2.35 (m, 2 H), 2.36-2.45 (m, 2 H), 3.44-3.48 (m, 1 H), 3.48-3.56 (m, 2 H), 3.69 (ddd, J=13.8, 8.9, 5.3 Hz, 2 H), 4.77 (s, 2 H), 7.12 (t, J=7.6 Hz, 1 H), 7.39 (d, J=7.0 Hz, 1 H), 7.51 (d, J=7.9 Hz, 1 H), 7.74 (dd, J=8.1, 5.3 Hz, 1 H), 8.37 (dt, J=8.0, 1.6 Hz, 1 H), 8.65 (d, J=4.6 Hz, 1 H), 8.96 (s, 1 H); MS (APCI) m/z 314 (M+H)+. Anal. Calcd. for C21H19N3.2.85 TFA: C, 50.24; H, 3.45; N, 6.58. Found: C, 49.97; H, 3.54; N, 6.80.

Provenance & Evidence