Methyl vinyl sulfone → 5-Bromo-1-[2-(methylsulfonyl)ethyl]-2(1H)-pyridinone
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.[CH3:9][S:10]([CH:13]=[CH2:14])(=[O:12])=[O:11]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:14][CH2:13][S:10]([CH3:9])(=[O:12])=[O:11])[CH:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
5-Bromopyridin-2-ol (4.0 g, 23.0 mmol) and methylsulfonylethene (2.4 g, 2.0 mL, 23.0 mmol) were combined in N,N-dimethylformamide (DMF, 23 mL) and heated to 100° C. The crude reaction mixture was then evaporated to dryness. The crude material was then dissolved in a minimum of dichloromethane. The solution was then washed twice with an aqueous 1 M solution of hydrochloric acid, two times with a saturated aqueous solution of sodium bicarbonate, two times with a saturated aqueous solution of sodium chloride, and finally by two washes of water. The organic layer was dried over sodium sulfate and then evaporated to dryness to yield the product as a pale brown solid (1.87 g, 6.68 mmol, 29%). ESI-MS m/z calc. 279.0. found 280.0 (M+1)+. Retention time 0.34 minutes.
Workup
- customThe crude reaction mixture
- customwas then evaporated to dryness
- dissolutionThe crude material was then dissolved in a minimum of dichloromethane
- washThe solution was then washed twice with an aqueous 1 M solution of hydrochloric acid, two times with a saturated aqueous solution of sodium bicarbonate, two times with a saturated aqueous solution of sodium chloride
- dry with materialThe organic layer was dried over sodium sulfate
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-b8fb998449f846128933bcb6ed9cc48d
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969386B2
Reaction notes
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