Water → HCID 68154200, 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, 0.14 g, 0.32 mmol) was dissolved in dichloromethane (5 mL) and cooled to −78° C. Ethylmagnesium bromide (0.10 mL, 3 M diethyl ether solution, 0.32 mmol, equiv) was added dropwise and the mixture was stirred for 30 minutes at −78° C. Additional ethylmagnesium bromide (0.10 mL, 3 M diethyl ether solution, 0.32 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) and warmed to ambient temperature, poured into water 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 9.14 (1H, s), 8.46 (1H, d, J=2.4 Hz), 8.18 (1H, d, J=8.0 Hz), 7.84 (2H, d, J=8.7 Hz), 7.78 (1H, d, J=8.7 Hz), 7.73 (1H, m), 7.67-7.60 (2H, m), 7.53 (1H, t, J=7.7 Hz), 7.48 (2H, d, J=8.5 Hz), 7.43 (1H, br t, J=7.6 Hz), 7.38-7.33 (2H, m), 6.53 (1H, m), 5.78 (2H, s), 5.12 (1H, d, J=4.7 Hz), 4.73-4.68 (1H, m), 1.71-1.64 (1H, m), 1.5-1.43 (1H, m), 0.78 (3H, t, J=7.4 Hz) ppm; high resolution mass spectrometry (ES+) m/z 476.2061 [(M+H)+; calculated for C29H26N5O2: 476.2081].

Provenance & Evidence