Ethylene Glycol → HCID 86670438, compound

HRID 1972686Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([SH:8])=[N:6][CH:7]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][N:11]=1.C(=O)([O-])[O-].[K+].[K+].C(O)CO>[Cu](I)I.CC(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:13]2[CH:12]=[N:11][C:10]([Cl:9])=[CH:15][CH:14]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

5-Bromo-2-pyridinethiol (633 mg, 3.33 mmol, Combi-Blocks, Inc., San Diego, Calif.), 2-chloro-5-iodopyridine (798 mg, 3.33 mmol, Sigma-Aldrich, St. Louis, Mo.), copper iodide (32 mg, 0.17 mmol, Strem Chemical Inc, Newburyport, Mass.), potassium carbonate (921 mg, 6.67 mmol), ethylene glycol (0.37 mL, 6.67 mmol), and 2-propanol (8 mL) were added to a reaction vial. The vial was sealed, purged with nitrogen for several minutes, and heated at 80° C. for 16 h. After cooling to room temperature, the solvents were removed under vacuum. The residue was absorbed onto a plug of silica gel and purified by chromatography through a silica gel column (40 g), eluting with a gradient of 0% to 10% EtOAc in hexanes, to provide 5-bromo-2-((6-chloro-3-pyridinyl)sulfanyl)pyridine (318 mg) as a white solid.

Workup

customThe vial was sealed
custompurged with nitrogen for several minutes
temperatureAfter cooling to room temperature
customthe solvents were removed under vacuum
customThe residue was absorbed onto a plug of silica gel
custompurified by chromatography through a silica gel column (40 g)
washeluting with a gradient of 0% to 10% EtOAc in hexanes

Sources & evidence

ORD record: ord-47e7b928de074eecaed6a43a09404c0c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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