Ethylene Glycol → HCID 86670383, compound

Temperature

80 °C

2-Chloro-5-iodopyridine (1.11 g, 4.64 mmol, Sigma-Aldrich, St. Louis, Mo.), 4-bromothiophenol (0.88 g, 4.64 mmol, Sigma-Aldrich, St. Louis, Mo.), copper iodide (44 mg, 0.23 mmol, Strem Chemical Inc, Newburyport, Mass.), potassium carbonate (1.28 g, 9.29 mmol), ethylene glycol (0.52 mL, 9.29 mmol), and iPrOH (10 mL) were added to a reaction vial. The vial was closed, purged with nitrogen for several minutes, and heated at 80° C. for 16 h. After cooling to room temperature, the reaction mixture was diluted with water (10 mL) and extracted with CH2Cl2 (20 mL) and then EtOAc (20 mL). The combined organic extracts were combined and the solvents were removed under reduced pressure. The residue was absorbed onto a plug of silica gel and purified by column chromatography (24 g of silica gel, 0 to 10% EtOAc in hexanes), to provide 5-((4-bromophenyl)sulfanyl)-2-chloropyridine (1.17 g) as white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.41 (d, J=2.54 Hz, 1H), 7.81 (dd, J=2.54, 8.41 Hz, 1H), 7.57-7.61 (m, 2H), 7.54 (d, J=8.41 Hz, 1H), 7.30-7.35 (m, 2H); m/z (ESI, +ve ion) 300.0 (M+H)+.

1. customThe vial was closed
2. custompurged with nitrogen for several minutes
3. temperatureAfter cooling to room temperature
4. additionthe reaction mixture was diluted with water (10 mL)
5. extractionextracted with CH2Cl2 (20 mL)
6. customthe solvents were removed under reduced pressure
7. customThe residue was absorbed onto a plug of silica gel
8. custompurified by column chromatography (24 g of silica gel, 0 to 10% EtOAc in hexanes)

ORD record

ord-b6933e11398141c9a850a8b1354cf4f8

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08431563B2