Cl[C:2]1[C:11]2=[N:12][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14]([CH3:15])=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.C([O-])=O.[NH4+].C(O)C>[Pd].C(#N)C>[CH3:15][C:14]1[N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]=[C:11]2[C:10]=1[C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:3]=[CH:2]24-Chloro-1-methyl-2-phenyl-2H-pyrazolo[3,4-c]quinoline (250 mg, 0.85 mmol) was combined with ammonium formate (268 mg, 4.25 mmol), ethanol (4 mL), and palladium on carbon (10%, 25 mg). The resulting gray suspension was warmed to 60° C. and stirred at this temperature for 18 hours. The reaction was cooled to ambient temperature and filtered through CELITE filter agent. The methanol was removed under reduced pressure and the resulting material was purified by automated flash chromatography (AnaLogix, eluted with a gradient of 0-30% CMA in chloroform) to provide material that was stirred in acetonitrile. A solid was isolated by filtration to provide 40 mg of 1-methyl-2-phenyl-2H-pyrazolo[3,4-c]quinoline as a white powder, mp 128-130° C. MS (APCI) m/z 260 (M+H)+; Anal. calcd for C17H13N3.0.15H2O: C, 77.93; H, 5.12; N, 16.04. Found: C, 78.09; H, 5.51; N, 16.27.
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