[Cl:1][C:2]1[CH:18]=[N:17][CH:16]=[CH:15][C:3]=1[C:4]([NH:6][NH:7][C:8]1[CH:13]=[C:12]([I:14])[CH:11]=[CH:10][N:9]=1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[Si](N=[N+]=[N-])(C)C.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:18]=[N:17][CH:16]=[CH:15][C:3]=1[C:4]1[N:9]2[CH:10]=[CH:11][C:12]([I:14])=[CH:13][C:8]2=[N:7][N:6]=1To a mixture of 3-chloro-N′-(4-iodopyridin-2-yl)isonicotinohydrazide (1.53 g, 4.08 mmol) and polymer supported triphenyl phosphine (2.83 g, 6.19 mmol) in tetrahydrofuran (35 mL) was added trimethylsilylazide (0.82 mL, 6.20 mmol) and a 40% solution of diethyl azodicarboxylate in toluene (3.40 mL, 7.42 mmol) and it was stirred in an orbital stirrer at room temperature for 2.5 hours. The mixture was filtered and rinsed with ethyl acetate, concentrated under reduced pressure and the resulting crude was purified by flash chromatography eluting with hexanes:isopropyl alcohol (3:2) to give the title compound (0.80 g, 55%) as a yellowish solid.
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