[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]1([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([NH:22][CH:23]([CH3:25])[CH3:24])[CH:14]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl>C(COC)OC>[C:5]1([C:11]2[N:1]=[N:2][NH:3][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([NH:22][CH:23]([CH3:25])[CH3:24])[CH:14]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1Add sodium azide (0.13 g) to a solution of 1-phenyl-2-(3-(isopropylamino)-4-nitrophenyl)acetylene (0.56 g) in dimethoxyethane (5 mL). Heat to reflux for 2 hours. Cool to room temperature. Add 1N hydrochloric acid (10 mL), extract with ethyl acetate (20 mL), and wash with saturated aqueous sodium chloride (2×10 mL). Dry organic phase over sodium sulfate and concentrate under reduced pressure. Subject the reside to silica gel chromatography, eluting with 1:1 ethyl acetate:hexane to provide the desired compound as a yellow solid (0.51 g, 80%).
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