Sodium Azide → 4-Azido-6-bromo-2-chloro-3-(difluoromethoxy)pyridine

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4,6-Dibromo-2-chloro-3-(difluoromethoxy)pyridine (780 mg, 2.312 mmol) was dissolved in DMF (5 mL), and sodium azide (180 mg, 2.77 mmol) was added. The reaction mixture was heated at 65° C. for 2 h and the progress of the reaction was checked by liquid chromatography-mass spectrometry (LC-MS). The reaction appeared to be mostly complete. The product was partitioned between Et2O and H2O. The aqueous phase was then extracted twice more with Et2O. The organic extracts were combined, diluted with petroleum ether, washed twice with H2O, dried, and concentrated. The product was purified by column chromatography (SiO2, EtOAc/hexane gradient) to yield 4-azido-6-bromo-2-chloro-3-(difluoromethoxy)-pyridine (0.335 g, 48.4%): 1H NMR (300 MHz, CDCl3) δ 7.26 (s, 1H), 6.59 (t, J=73.6, 1H).

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