[OH:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([O:10][CH3:11])=[N:4][CH:3]=1.[Cl:12][C:13]1[N:14]=[CH:15][C:16]2[C:21]([C:22]=1[CH2:23]Cl)=[CH:20][CH:19]=[CH:18][CH:17]=2.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:12][C:13]1[N:14]=[CH:15][C:16]2[C:21]([C:22]=1[CH2:23][O:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([O:10][CH3:11])=[N:4][CH:3]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2A mixture of 5-hydroxy-2-methoxyisonicotinaldehyde (73 mg, 0.48 mmol, 1 eq.), 3-chloro-4-(chloromethyl)isoquinoline (crude above, 0.48 mmol), and K2CO3 (265 mg, 1.92 mmol, 4 eq.) in DMF (2.0 mL) was heated at 60° C. for 1 h. The mixture was cooled, filtered, concentrated to dryness. The crude was purified on silica gel using a mixture of EtOAc and hexanes to give 5-((3-chloroisoquinolin-4-yl)methoxy)-2-methoxyisonicotinaldehyde (22 mg, 14%) as an yellow solid. 1H NMR (400 MHz; CDCl3) δ=10.19 (s, 1H), 9.05 (s, 1H), 8.23 (s, 1H) 8.06 (d, 1H), 7.98 (d, 1H), 7.76 (t, 1H), 7.63 (t, 1H), 7.01 (s, 1H), 5.72 (s, 2H), 3.87 (s, 3H). LRMS (M+H+) m/z 329.1.
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