Sodium hydride → HCID 90313196, compound

Temperature

0 °C

To a 100 mL reaction tube, equipped with a reflux condenser and under a nitrogen atmosphere, was added a solution consisting of tetrahydro-2H-thiopyran-4-ol (1.04 g, 8.78 mmol) in DMF (2 mL). The mixture was cooled to the 0° Celsius, and then treated with NaH (0.540 g, 60% dispersion in mineral oil, 13.5 mmol). When the addition was complete, the reaction was warmed to rt and stirred 30 min before adding 3-bromo-2-chloropyridine (1.3 g, 6.8 mmol), and heating at 130° Celsius for 10 hours. The reaction mixture was cooled to rt and carefully quenched with H2O, concentrated to remove the solvent, and extracted with water (20 mL) and EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated to dryness. The crude material was purified by FCC to provide the title compound.

1. customTo a 100 mL reaction tube
2. customequipped with a reflux condenser and under a nitrogen atmosphere
3. additionwas added a solution
4. additionWhen the addition
5. temperaturethe reaction was warmed to rt
6. temperatureheating at 130° Celsius for 10 hours
7. temperatureThe reaction mixture was cooled to rt
8. customcarefully quenched with H2O
9. concentrationconcentrated
10. customto remove the solvent
11. extractionextracted with water (20 mL) and EtOAc (3×20 mL)
12. dry with materialThe combined organic extracts were dried over Na2SO4
13. filtrationfiltered
14. concentrationconcentrated to dryness
15. customThe crude material was purified by FCC

ORD record

ord-3f72b04b4cf44690b3fc1017929eb8f4

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079866B2