Sodium Carbonate → 2-(Pyridin-3-Yl)Benzaldehyde
Reaction equation
Br[C:2]1([CH:9]=[CH:8][CH:7]=[CH:6][CH2:5]1)[CH:3]=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[N:16]1[CH:21]=[CH:20][CH:19]=[C:18](B(O)O)[CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[CH:3]=[O:4])[CH:17]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 110 °C
Procedure
To a suspension of 1-bromobenzaldehyde (250 μL, 2.14 mmol), sodium carbonate (270 mg, 2.55 mmol), and 3-pyridineboronic acid (289 mg, 2.35 mmol) in 4.2 mL of N,N-dimethylformamide/water (2:1) were added palladium acetate (24 mg, 0.11 mmol) and triphenylphosphine (115 mg, 0.44 mmol) under nitrogen. After being stirred at 110° C. overnight, the reaction mixture was filtered. The filtrate was diluted with chloroform, and the solution was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (chloroform/methanol=99/1 to 95/5) to obtain the title compound as a white powder (250 mg, 64%).
Workup
- filtrationthe reaction mixture was filtered
- additionThe filtrate was diluted with chloroform
- washthe solution was washed with brine
- dry with materialdried over MgSO4
- filtrationAfter filtration
- concentrationthe filtrate was concentrated in vacuo
- customthe residue was purified by silica gel column chromatography (chloroform/methanol=99/1 to 95/5)
Sources & evidence
- ORD record
- ord-116ce200533745c88f537710052355d5
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962674B2
Reaction notes
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