N,N'-Dimethylethylenediamine → 5-(Methylsulfonyl)pyridine-2-carbonitrile
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH3:10][S:11]([O-:13])=[O:12].[Na+].CNCCNC>CS(C)=O.[Cl-].[NH4+].[O-]S(C(F)(F)F)(=O)=O.[Cu+2].[O-]S(C(F)(F)F)(=O)=O>[CH3:10][S:11]([C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1)(=[O:13])=[O:12]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 115 °C
Procedure
To a solution of 5-bromo-pyridine-2-carbonitrile (500 mg, 2.73 mmol) in DMSO (10 mL) in a microwave tube was added 85% sodium methanesulfinate (525 mg, 4.37 mmol) followed by copper (II) triflate (990 mg, 2.74 mmol) and dimethylethylene diamine (890 μL, 8.36 mmol). The mixture was warmed in a microwave reactor at 115° C. After 30 minutes, the mixture was diluted with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with saturated aqueous ammonium chloride (2×15 mL), brine (3×15 mL), dried over magnesium sulfate, filtered and concentrated. The crude material was triturated with ether to afford 5-methanesulfonyl-pyridine-2-carbonitrile.
Workup
- extractionextracted with ethyl acetate (3×20 mL)
- washThe combined organic layers were washed with saturated aqueous ammonium chloride (2×15 mL), brine (3×15 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude material was triturated with ether
Sources & evidence
- ORD record
- ord-2eb84b8fe36f45bfa12f8d71c36d34b6
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063065B2
Reaction notes
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