[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13]I)[N:12]=2)=[CH:4][CH:3]=1.[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C=O)C.CCOC(C)=O>[N:15]([CH2:13][C:11]1[N:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[O:9][CH:10]=1)=[N+:16]=[N-:17]A solution of 2-(4-fluorophenyl)-4-(iodomethyl)oxazole (1.2 g, 3.96 mmol) in dry DMF (10 mL) was added sodium azide (515 mg, 7.9 mmol) and the reaction mixture was heated to 70° C. for 8 h. The reaction mixture was allowed to cool down to room temperature and diluted with EtOAc. The mixture was extracted with EtOAc and the combined extracts were washed with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 4-(azidomethyl)-2-(4-fluorophenyl)oxazole (0.73 g, yield 85%) as a pale orange liquid, which was carried through without further purification. 1H NMR (400 MHz, CDCl3) δ 8.04-8.01 (m, 2H), 7.67 (s, 1H), 7.16-7.12 (m, 2H), 4.34 (s, 2H). MS (ESI) m/z: Calculated for C10H7FN4O: 218.06. found: 219.2 (M+H)+.
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