Sodium hydride → 2,5-Bis{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one

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5-{[4-(1H-Pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (Example 406, 71 mg, 0.21 mmol) was suspended in degassed N,N-dimethylformamide (3 mL), cooled to 0° C. and sodium hydride (17 mg, 0.42 mmol, 2 equiv, 60% dispersion in mineral oil) was added. After stirring for 10 minutes at 0° C., the mixture was warmed to ambient temperature and stirred for 45 minutes. 1-[4-(Bromomethyl)phenyl]-1H-pyrazole (74 mg, 0.31 mmol, 1.5 equiv) was added, the mixture as stirred for 2 hours and then poured into sodium bicarbonate (30 mL, aqueous saturated) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 88:12; dichloromethane:methanol), providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 9.09 (1H, s), 8.45-8.44 (2H, m), 8.15 (1H, d, J=7.8 Hz), 7.82-7.78 (4H, m), 7.75-7.72 (2H, m), 7.57 (1H, t, J=7.8 Hz), 7.48 (1H, t, J=7.7 Hz), 7.45-7.40 (4H, m), 6.52 (2H, s), 5.75 (2H, s), 5.14 (2H, s) ppm; high resolution mass spectrometry (ES+) m/z 498.2063 [(M+H)+; calculated for C30H24N7O: 498.2037].

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