[CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[CH:5][C:4]=1[O:11][CH2:12][C:13]1[C:14]([C:19]#[N:20])=[N:15][CH:16]=[CH:17][CH:18]=1)=[O:2].[N-:21]=[N+:22]=[N-:23].[Na+].O>ClC1C=CC=CC=1>[N:20]1[NH:21][N:22]=[N:23][C:19]=1[C:14]1[C:13]([CH2:12][O:11][C:4]2[C:3]([CH:1]=[O:2])=[CH:8][C:7]([O:9][CH3:10])=[N:6][CH:5]=2)=[CH:18][CH:17]=[CH:16][N:15]=1To TEA hydrochloride salt (123 mg, 0.89 mmol, 4 equiv.) and 3-((4-formyl-6-methoxypyridin-3-yloxy)methyl)picolinonitrile (70 mg, 0.26 mmol, 1 equiv.) in chlorobenzene (5.0 mL) was added NaN3 (48 mg, 0.89 mmol, 4 equiv.) at rt. The mixture was heated to 110° C. for 2 h, cooled to rt, and added water (5.0 mL). The precipitate was filtered and washed with EtOAc and water and dried under high vacuo to give 5-((2-(2H-tetrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde as a white solid. 1H NMR (400 MHz; DMSO) δ=10.23 (s, 1H), 8.61 (d, 1H), 8.16 (s, 1H), 8.10 (d, 1H), 7.38 (dd, 1H), 6.96 (s, 1H) 5.73 (s, 2H), 3.83 (s, 3H). LRMS (M+H+) m/z 313.0.
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