Water → HCID 68154041, compound

Participants

Reaction Conditions

Reaction Steps

2-(3-Oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)benzaldehyde (Example 529, 76 mg, 0.17 mmol) was dissolved in dichloromethane (5 mL) and cooled to −78° C. Methylmagnesium bromide (0.057 mL, 3 M diethyl ether solution, 0.17 mmol, 1 equiv) was added dropwise and the mixture was stirred for 30 minutes at −78° C. Additional methylmagnesium bromide (0.057 mL, 3 M diethyl ether solution, 0.17 mmol, 1 equiv) was added and the mixture was stirred for an additional 30 minutes at −78° C. The mixture was treated with sodium bicarbonate (3 mL, aqueous saturated), warmed to ambient temperature, poured into water (10 mL) and extracted with dichloromethane (3×50 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified via silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate; then 100:0 to 0:100; ethyl acetate:ethyl acetate containing 5% methanol), providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 9.13 (1H, s), 8.45 (1H, d, J=2.4 Hz), 8.18 (1H, d, J=8.0 Hz), 7.83 (2H, d, J=8.6 Hz), 7.78 (1H, d, J=8.8 Hz), 7.73 (1H, d, 1.1 Hz), 7.70 (1H, d, J=7.8 Hz), 7.65-7.60 (1H, m), 7.54 (1H, t, J=7.7 Hz), 7.48 (2H, d, 8.3 Hz), 7.44 (1H, d, J=7.8 Hz), 7.39-7.31 (2H, m), 6.53 (1H, m), 5.78 (2H, s), 5.19 (1H, d, J=4.2 Hz), 4.94-4.88 (1H, m), 1.27 (3H, d, J=6.4 Hz) ppm; high resolution mass spectrometry (ES+) m/z 462.1906 [(M+H)+; calculated for C29H24N5O2: 462.1925].

Provenance & Evidence