Iodoethane → 2-Chloro-5-ethoxy-4-iodopyridine

6-Chloro-4-iodo-pyridin-3-ol (0.41 g, 1.62 mmol) was dissolved in anhydrous DMF (4 mL) and stirred at room temperature. Potassium carbonate (0.67 g, 4.9 mmol) and iodoethane (0.40 mL, 4.9 mmol) were added sequentially. The mixture was heated to 60° C. and maintained for 2 hours. The mixture was cooled to room temperature and filtered. The filtrate was diluted with diethyl ether (25 mL) and washed with 20% aqueous citric acid (25 mL). The aqueous was extracted with diethyl ether (2×20 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was triturated with hexane resulting in a tan solid (0.42 g, 91%). 1H NMR (400 MHz, CDCl3): δ 7.80 (s, 1H), 7.74 (s, 1H) 4.18 (q, J=7.1 Hz, 2H), 1.51 (t, J=7.1 Hz, 3H).

1. temperatureThe mixture was heated to 60° C.
2. temperaturemaintained for 2 hours
3. temperatureThe mixture was cooled to room temperature
4. filtrationfiltered
5. additionThe filtrate was diluted with diethyl ether (25 mL)
6. washwashed with 20% aqueous citric acid (25 mL)
7. extractionThe aqueous was extracted with diethyl ether (2×20 mL)
8. washThe combined organics were washed with brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. customThe residue was triturated with hexane resulting in a tan solid (0.42 g, 91%)

ORD record

ord-9252221591134caeaf40ef5a6213aea6

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07151105B2