Cesium carbonate → Methyl 5-(6-(3-ethylureido)pyridin-3-yl)-2-oxo-1,2-dihydropyridine-3-carboxylate
Reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10](B2OC(C)(C)C(C)(C)O2)=[CH:9][N:8]=1)=[O:5])[CH3:2].I[C:23]1[CH:24]=[C:25]([C:30]([O:32][CH3:33])=[O:31])[C:26](=[O:29])[NH:27][CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[CH2:1]([NH:3][C:4](=[O:5])[NH:6][C:7]1[N:8]=[CH:9][C:10]([C:23]2[CH:24]=[C:25]([C:30]([O:32][CH3:33])=[O:31])[C:26](=[O:29])[NH:27][CH:28]=2)=[CH:11][CH:12]=1)[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of N-ethyl-N′-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)urea (Intermediate 1, 200 mg, 0.69 mmol), methyl 5-iodo-2-oxo-1,2-dihydro-3-pyridinecarboxylate (174 mg, 0.62 mmol), Tetrakispalladium (72.2 mg, 0.06 mmol), and cesium carbonate (224 mg, 0.69 mmol) in dioxane (4 mL) and water (1.000 mL) was heated to 100° C. in microwave for 1 h. The reaction mixture was filtered through Celite and washed with methanol. The resulting solution was concentrated under reduced pressure to give a yellow solid. The solid was triturated with acetone, then collected by filtration and added to hot acetone/water. The solution was cooled to room temperature, and the solid that formed was collected by filtration and placed under high vacuum to remove residual solvent (58 mg). MS (ESP): 317 (M+H+) for C15H16N4O4.
Workup
- filtrationThe reaction mixture was filtered through Celite
- washwashed with methanol
- concentrationThe resulting solution was concentrated under reduced pressure
- customto give a yellow solid
- customThe solid was triturated with acetone
- filtrationcollected by filtration
- additionadded to hot acetone/water
- customthe solid that formed
- filtrationwas collected by filtration
- customto remove residual solvent (58 mg)
Sources & evidence
- ORD record
- ord-95249974426848dbbfe8f5d14d407fa5
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07674801B2
Reaction notes
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