2-Methyl-5-vinylpyridine → 7-[(E)-2-(6-methylpyridin-3-yl)vinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

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A mixture of bis(tri-t-butylphosphino)palladium (26.3 mg, 0.052 mmol; Aldrich), the product of Example 1C (123 mg, 0.52 mmol), sodium t-butoxide (124 mg, 1.29 mmol; Aldrich) and the product of Example 1B (150 mg, 0.52 mmol) was combined with 1,4-dioxane (3 mL). The mixture was purged with a stream of nitrogen for 2 minutes, then heated at 105° C. for 6 hours in a sealed tube. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was dissolved in dimethyl sulfoxide (5 mL), filtered through a glass microfiber frit and purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 40-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (400 MHz, methanol-d4) δ ppm 2.05-2.15 (m, 4 H), 2.54 (s, 3 H), 3.02-3.12 (m, 2 H), 3.14 (pent, J=3.6 Hz, 1 H), 3.20-3.29 (m, 2 H), 4.23 (s, 2 H), 7.02 (t, J=7.6 Hz, 1 H), 7.23 (d, J=16.5 Hz, 1 H), 7.24-7.27 (m, 1 H), 7.31 (d, J=8.2 Hz, 1 H), 7.39 (d, J=7.3 Hz, 1 H), 7.68 (d, J=16.5 Hz, 1 H), 8.01 (dd, J=8.2, 2.4 Hz, 1 H), 8.61 (d, J=2.4 Hz, 1 H); MS (APCI) m/z=330 (M+H)+.

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