Br[CH2:2][C:3]1[C:15]([C:16]#[N:17])=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[C:5]([O:18][CH2:19][CH3:20])[CH:4]=1.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N:21]([CH2:2][C:3]1[C:15]([C:16]#[N:17])=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[C:5]([O:18][CH2:19][CH3:20])[CH:4]=1)=[N+:22]=[N-:23]After dissolving tert-butyl 4-(bromomethyl)-5-cyano-2-ethoxybenzoate (2.20 g, 70% purity) in dimethylformamide (25 ml), sodium azide (2.1 g) was added and the mixture was stirred at 50° C. for 30 minutes. It was then diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated to yield the title compound (1.913 g).
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