C[C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6](O)[C:5]=2[NH:4][CH:3]=1.[C:16]([O-:19])([O-])=O.[Cs+].[Cs+].[CH2:22](Br)[CH:23]=C.[CH2:26]1COCC1>CN1C(=O)CCC1>[CH2:10]([CH:9]1[CH:16]([OH:19])[C:5]23[N:4]=[CH:3][CH:2]=[C:14]2[CH:13]=[CH:12][CH:11]=[C:6]3[N:7]([CH3:26])[CH2:8]1)[CH:22]=[CH2:23]A solution of 1-methyl-3H-pyrrolo[2,3-c]quinolin-4-ol (1.2 g, 6.05 mmol) in a mixture of THF (30 mL) and NMP (60 mL) was treated with Cs2CO3 (2.95 g, 9.08 mmol). Allyl bromide (0.524 mL, 6.06 mmol) was added dropwise, and the resulting mixture was stirred at 40° C. for 12 h. The mixture was cooled and quenched with aqueous HCl (1 N) and EtOAc. The organic layer was separated, washed with aqueous HCl (1 N), brine, and dried over Na2SO4. Filtration and removal of the volatiles gave a residue that was triturated with Et2O to give the title compound (0.78 g, 54%) as a solid. LCMS (ES+) m/z 239 (M+H)+.
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