Sodium Carbonate → 7-(quinolin-3-yl)-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A suspension of the product of Example 1B (150 mg, 0.52 mmol), 3-quinolineboronic acid (102 mg, 0.59 mmol; Aldrich), dichlorobis(triphenylphosphine)palladium (II) (18 mg, 0.026 mmol; Aldrich) and 1.0 M sodium carbonate (1.3 mL) in 2-propanol (3.8 mL) was purged with nitrogen and then stirred at 80° C. for 1 hour in a sealed tube. The reaction mixture was cooled and partitioned between CHCl3 (2×30 mL) and 1.0 M sodium carbonate (50 mL). The combined organic extracts were dried (sodium sulfate) and concentrated under vacuum. The resulting residue was purified by reverse-phase HPLC [Waters XBridge™RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 40-100% 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 1.98-2.16 (m, 4 H), 3.02-3.14 (m, 3 H), 3.25 (ddd, J=14.1, 8.8, 5.5 Hz, 2 H), 4.28 (s, 2 H), 7.12-7.22 (m, 2 H), 7.39 (dd, J=7.3, 1.5 Hz, 1 H), 7.66 (ddd, J=8.1, 7.0, 1.1 Hz, 1 H), 7.79 (ddd, J=8.5, 6.9, 1.4 Hz, 1 H), 8.03 (dd, J=8.2, 0.9 Hz, 1 H), 8.09 (d, J=8.5 Hz, 1 H), 8.57 (d, J=2.1 Hz, 1 H), 9.09 (d, J=2.1 Hz, 1 H); MS (ESI+) m/z 340 (M+H)+.

Herkunft & Nachweise