(+-)-3-Quinuclidinol → HCID 11450046, compound

Participants

Reaction Steps

3-Quinuclidinol (Aldrich, 254 mg, 2 mmol) was coupled with 3-(6-chloropyridazin-3-yl)-1H-indole (Bionet, 458 mg, 2 mmol) at 60° C. for 16 hours according to the procedure of Example 7A. The title compound was purified by preparative HPLC (Xterra™, column, Xterra RP-18, 5 μm, 30×100 mm. Eluting Solvent, MeCN/H2O (NH4HCO3, 0.1 M, pH=10), (v. 90/10 to 10/90 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) as solid (400 mg, 63%). 1H NMR (MeOH-D4, 300 MHz) 1.50-1.64 (m, 1H), 1.71-1.93 (m, 2H), 2.00-2.15 (m, 1H), 2.29-2.36 (m, 1H), 2.78-3.04 (m, 5H), 3.43-3.55 (m, 1H), 5.24-5.32 (m, 1H), 7.12-7.25 (m, 3H), 7.42-7.48 (m, 1H), 7.87 (s, 1H), 8.01 (d, J=9.2 Hz, 1H), 8.26-8.33 (m, 1H) ppm. MS (DCI/NH3) m/z 321 (M+H)+.

Provenance & Evidence