Potassium Carbonate → 5-Bromo-6-methylpyridine-3-carbaldehyde
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([O:11]C)=O)[CH:5]=[N:6][C:7]=1I.[C:13]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[O:11])[CH:5]=[N:6][C:7]=1[CH3:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 110 °C
Procedure
To a mixture of methyl 5-bromo-6-iodo-3-pyridinecarboxylate (232 mg, 0.679 mmol), tetrakis(triphenylphosphine)palladium (0) (39.2 mg, 0.034 mmol), and K2CO3 (281 mg, 2.036 mmol) in dioxane (5 ml), trimethylboroxin (0.095 ml, 0.679 mmol) was added under N2. The reaction mixture was heated at 110° C. and more tetrakis(triphenylphosphine)palladium (0) was added in several portions until starting material was not detected by HPLC. The reaction mixture was diluted with water and extracted three times with EtOAc. The combined organic phases were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude of reaction was purified by flash chromatography using Flashmaster II, a 5 g silica gel cartridge, and mixtures of hexane and EtOAc to afford the title compound (75 mg, 48%) as a yellow solid.
Workup
- additionwas added under N2
- extractionextracted three times with EtOAc
- washThe combined organic phases were washed with brine
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated under reduced pressure
- customThe crude of reaction
- customwas purified by flash chromatography
Sources & evidence
- ORD record
- ord-f2aa4450e4574b9cbd11d4253020670d
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08097628B2
Reaction notes
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