Cl[CH2:2][C:3]1[C:4]([CH3:13])=[N:5][C:6]([CH3:12])=[C:7]([C:9]([CH3:11])=[CH2:10])[CH:8]=1.[N-:14]=[N+:15]=[N-:16].[Na+].O.CCOC(C)=O>CN(C=O)C>[N:14]([CH2:2][C:3]1[C:4]([CH3:13])=[N:5][C:6]([CH3:12])=[C:7]([C:9]([CH3:11])=[CH2:10])[CH:8]=1)=[N+:15]=[N-:16]A mixture of 96.5 mg of the 3-(chloromethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)pyridine and 86.8 mg (1.34 mmol) of NaN3 in 3 mL of DMF was heated at 70° C. for 4 h. Water and EtOAc were added, and the layers were separated. The organic layer was washed with H2O (2×) and then with brine. It was dried over Na2SO4, filtered, and concentrated to give the crude azide (3-(azidomethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)pyridine) which was used without further purification.
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