[CH2:1]([O:5][C:6]1[N:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:9]=1[C:10]([C:16]([CH3:18])=[CH2:17])=[N:11]2)[CH2:2][CH2:3][CH3:4]>[Pd]>[CH2:1]([O:5][C:6]1[N:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:9]=1[C:10]([CH:16]([CH3:18])[CH3:17])=[N:11]2)[CH2:2][CH2:3][CH3:4]1-butoxy-9-fluoro-6-isopropenylbenzo[c]-1,6-naphthyridine (50 mg, 0.161 mmol) and 5% Pd on Carbon; Type A470129-5® (Johnson Matthey) (5 mg, 0.161 mmol) were combined in a vial. The vial was flushed with nitrogen for several minutes, and then EtOH (1.0 ml) was added. The reaction mixture was stirred under hydrogen (balloon pressure) for 6 hr. The reaction mixture was flushed with nitrogen, diluted with EtOAc (5 mL), and then filtered through a syringe filter to remove Pd/C. The filtrate was concentrated, and the resulting residue was adsorbed on to silica gel, then purified by column chromatography on silica gel eluting with an EtOAc/hexanes gradient to afford 1-butoxy-9-fluoro-6-isopropylbenzo[c]-1,6-naphthyridine. LRMS (ESI) calc'd for (C19H21FN2O) [M+H]+, 313.2; found 313.1.
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