Potassium Carbonate → HCID 23511409, compound
Reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[CH:8][C:9]([CH3:12])=[N:10][CH:11]=2)[N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].BrCCC[CH2:23][N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34]>CN(C=O)C>[CH3:12][C:9]1[N:10]=[CH:11][C:6]([C:4]2[N:3]=[CH:2][N:1]([CH2:23][N:24]3[C:28](=[O:29])[C:27]4[C:26](=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:25]3=[O:34])[CH:5]=2)=[CH:7][CH:8]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 5-(1H-imidazol-4-yl)-2-methyl-pyridine (1 eq) in DMF was added potassium carbonate (4 eq) at room temperature under dry conditions. After heating the reaction mixture in a 80° C. oil bath for 1 hour, N-(4-bromobutyl)phtalimide (3.9 eq) was added to the mixture. The solution was left stirring in a 80° C. oil bath for 24 hours. Upon cooling, the reaction was filtered and the solid was washed with ethyl acetate. The filterate was diluted with ethyl acetate and washed with NH4Cl (sat.), H2O, NaCl (sat.), dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography using an initial solvent gradient of 97% DCM, 3% MeOH, and 0.1% TEA (1 L) to afford the product (37%). MH+(361)
Workup
- waitThe solution was left
- temperatureUpon cooling
- filtrationthe reaction was filtered
- washthe solid was washed with ethyl acetate
- additionThe filterate was diluted with ethyl acetate
- washwashed with NH4Cl (sat.), H2O, NaCl (sat.)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by flash chromatography
Sources & evidence
- ORD record
- ord-8cfff045941b49d3b725c79d75e321e0
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07332476B2
Reaction notes
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