2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 69935267, compound

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Reaction Steps

2-[5-(4-Fluorobenzyl)-3-oxo-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl]benzaldehyde (Example 786) (60 mg, 0.15 mmol) was dissolved in dichloromethane (3 mL), treated with sodium borohydride (7.4 mg, 0.20 mmol, 1.3 equiv) and stirred at ambient temperature for 24 hours. The mixture was washed with brine (5 mL), dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was dissolved in dichloromethane (3 mL), treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (56 mg, 0.25 mmol, 1.6 equiv) and stirred at ambient temperature for 3 hours. The mixture was concentrated in vacuo and the residue was purified by preparative reverse phase HPLC (eluting 80:20 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid), providing the title compound: 1H-NMR (400 MHz, CD3OD) δ 9.12 (1H, s), 8.19 (1H, d, J=7.9 Hz), 7.75 (1H, d, J=8.6 Hz), 7.66-7.60 (2H, m), 7.55-7.51 (1H, m), 7.44-7.38 (5H, m), 7.20 (2H, d, J=8.8 Hz), 5.73 (2H, s), 4.45 (2H, s), ppm; low resolution mass spectrometry (ES+) m/z 399.9 [(M+H)+; calculated for C24H18FN3O2: 400.1].

Provenance & Evidence