1H-1,2,4-Triazole → HCID 53632732, compound

HRID 1502648Notes

Reaction equation

[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[C:6]([C:9]1[CH:10]=[CH:11][C:12](Br)=[N:13][CH:14]=1)(=[O:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O.O>[C:6]([C:9]1[CH:10]=[CH:11][C:12]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[N:13][CH:14]=1)(=[O:8])[CH3:7]

Participants

Conditions

Temperature: 100 °C

Procedure

622 mg (corresponding to 9.00 mmol) of 1H-1,2,4-triazole was dissolved in 10 mL of dimethylformamide. Then, 600 mg (corresponding to 3.00 mmol) of 5-acetyl-2-bromopyridine and 1.24 g (corresponding to 9.00 mmol) of potassium carbonate were added thereto. The resulting solution was heated at 100° C. for 3 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, supplemented with a saturated ammonium chloride aqueous solution and water, and extracted 3 times with dichloromethane. The combined dichloromethane layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (elution solvent: dichloromethane/ethyl acetate=4/1), to obtain 480 mg (corresponding to 2.55 mmol) of 5-acetyl-2-(1H-1,2,4-triazole-1-yl)pyridine (FIG. 4, step 1).

Workup

customAfter the completion of the reaction
temperaturethe reaction solution was cooled down to room temperature
extractionextracted 3 times with dichloromethane
washThe combined dichloromethane layer was washed with water
dry with materiala saturated saline solution, dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting crude product was purified by silica gel column chromatography (elution solvent: dichloromethane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-cc77916e3ab44b18a0ca0ebf1fd57f7f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09211350B2

Reaction notes

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