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A dry, 100 mL one neck round bottom flask was charged with 6-fluoro-2-iodopyridin-3-ol (2.59 ml, 11.9 mmol), a stirbar, and 50 mL dry DCE. The flask was fitted with an inert atmosphere/vacuum inlet, and the flask was cooled with a ice-water bath. The solution was carefully evacuated to <5 mm Hg, and refilled with nitrogen. The slurry was treated with triethylamine (2.49 ml, 17.9 mmol). To the stirring solution was added 2-methoxyethoxymethyl chloride (1.93 g, 15.5 mmol) dropwise over 30 minutes via syringe pump. The reaction was stirred for 2 h at 0° C., and then treated with 1 mL MeOH. The slurry was filtered cold, and the precipitate was washed with cold DCE (2×50 mL). The combined filtrates were concentrated in vacuo, and heated into 50 mL toluene. The slurry was cooled to room temperature, and then to −5° C. (refrigerator) overnight. The slurry was filtered, and the precipitate was washed with toluene (2×20 mL). The combined filtrates were concentrated in vacuo to afford 6-fluoro-2-iodo-3-((2-methoxyethoxy)methoxy)pyridine (3.91 g, 100% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 3.36 (s, 3H) 3.53-3.57 (m, 2H) 3.85-3.89 (m, 2H) 5.30 (s, 2H) 6.83 (dd, J=8.71, 3.62 Hz, 1H) 7.46 (dd, J=8.71, 6.46 Hz, 1H). 19F NMR (376 MHz, chloroform-d) δ ppm −74.58 (dd, J=5.85, 3.25 Hz, 1 F). 13C NMR (101 MHz, chloroform-d) δ ppm 59.01 (s, 1 C) 68.37 (s, 1 C) 71.39 (s, 1 C) 94.74 (s, 1 C) 106.51 (d, J=14.30 Hz, 1 C) 108.53 (d, J=38.15 Hz, 1 C) 126.55 (d, J=7.80 Hz, 1 C) 152.04 (d, J=4.77 Hz, 1 C) 156.71 (d, J=240.59 Hz, 1 C). HPLC-MS: 1.96 min (93.4%@215 nm; 97.2% @254 nm; m/z=327.9, calculated for C9H11FINO3+H+=328.1).

1. customThe flask was fitted with an inert atmosphere/vacuum inlet
2. temperaturethe flask was cooled with a ice-water bath
3. customThe solution was carefully evacuated to <5 mm Hg
4. additionrefilled with nitrogen
5. filtrationThe slurry was filtered cold
6. washthe precipitate was washed with cold DCE (2×50 mL)
7. concentrationThe combined filtrates were concentrated in vacuo
8. temperatureheated into 50 mL toluene
9. temperatureThe slurry was cooled to room temperature
10. customto −5° C.
11. custom(refrigerator) overnight
12. filtrationThe slurry was filtered
13. washthe precipitate was washed with toluene (2×20 mL)
14. concentrationThe combined filtrates were concentrated in vacuo