Ammonia → 5-{6-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]pyridazin-3-yl}-3-methyl-1H-indole

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Reaction Steps

The product of Example 10A (240 mg, 1 mmol) coupled with the product of Example 9A (250 mg, 1 mmol) according to the procedure in Example 8A, The title product was purified by preparative HPLC (Gilson, column, Symmetry® C-8 7 μm, 40×100 mm. Eluting Solvent, MeCN/H2O (with 0.2% v. TFA) (v. 90/10 to 10/90 over 20 min. flow rate, 75 mL/min., uv, 250 nm) as solid (40 mg, yield, 12%). 1H NMR (300 MHz, CD3OD) δ 1.50–1.64 (m, 1H), 1.69–1.92 (m, 2H), 2.01–2.14 (m, 1H), 2.29–2.35 (m, 1H), 2.37 (s, 3H), 2.81–3.04 (m, 5H), 3.43–3.55 (m, 1H), 5.27–5.34 (m, 1H), 7.06 (d, J=1.4 Hz, 1H), 7.24 (d, J=9.2 Hz, 1H), 7.44 (dd, J=8.5, 0.7 Hz, 1H), 7.71 (dd, J=8.8, 2.0, Hz, 1H), 8.07–8.12 (m, 2H) ppm. MS (DCl/NH3): m/z 335 (M+H)+.

Provenance & Evidence