Selenium Dioxide → HCID 21847939, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[Se](=O)=[O:18]>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[O:18])=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 135 °C
Procedure
A mixture of 200 mg (0.725 mmol) of l-(4-bromophenyl)-2-(4-pyridyl)-ethanone (from Step A) and 81 mg (0.725 mmol) of selenium(IV) oxide, and 5.5 mL of glacial acetic acid was heated to 135° C. for 2 h. After being cooled to room temperature, the reaction mixture was partitioned between saturated aqueous potassium carbonate and ethyl acetate. The aqueous layer was extracted twice more more with ethyl acetate. The organic layers were combined and washed with water and brine and dried over anhydrous sodium sulfate. Volatiles were removed under reduced pressure and the residue was flash chromatographed over silica gel (gradient elution 2-4% MeOH in DCM) to yield 100 mg of the titled compound, homogeous by TLC; mass spectrum (CI) m/e 290, 292 (M+1)+.
Workup
- temperatureAfter being cooled to room temperature
- customthe reaction mixture was partitioned between saturated aqueous potassium carbonate and ethyl acetate
- extractionThe aqueous layer was extracted twice more more with ethyl acetate
- washwashed with water and brine
- dry with materialdried over anhydrous sodium sulfate
- customVolatiles were removed under reduced pressure
- customchromatographed over silica gel (gradient elution 2-4% MeOH in DCM)
Sources & evidence
- ORD record
- ord-8222ba2d19fc40b6860c4891e9e5e7d5
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05955480
Reaction notes
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