Cesium carbonate → (6-Trifluoromethyl-pyridin-2-yl)-acetic acid ethyl ester
Reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7](P(C(C)(C)C)C(C)(C)C)(C)(C)[CH3:8].Br[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[N:22]=1.C([C:33](CC)([C:37]([O-:39])=[O:38])C([O-])=O)C.[Cl-].[NH4+]>COCCOC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:7]([O:39][C:37](=[O:38])[CH2:33][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[N:22]=1)[CH3:8]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 150 °C
Procedure
A mixture of caesium carbonate (1.87 g, 5.75 mmol) and tri-t-butylphosphine (107 μL, 0.44 mmol) in dry 1,2 dimethoxyethane (10 mL) was treated with tris-(dibenzylideneacetone)di-palladium (81 mg, 0.09 mmol), 2-Bromo-6-(trifluoromethyl)pyridine (1 g, 4.42 mmol) and diethylmalonate (0.8 mL, 5.3 mmol) under nitrogen atmosphere. The mixture was heated to 150° C. for 30 min in a microwave oven. After cooling to 20° C. the mixture was treated with a saturated solution of ammonium chloride (120 mL) and extracted with ethyl ether (3×80 mL). The organic phase was dried and evaporated to give a crude oil that was purified by flash chromatography eluting with n-hexane/ethyl ether 6/1.
Workup
- temperatureAfter cooling to 20° C. the mixture
- extractionextracted with ethyl ether (3×80 mL)
- customThe organic phase was dried
- customevaporated
- customto give a crude oil that
- customwas purified by flash chromatography
- washeluting with n-hexane/ethyl ether 6/1
Sources & evidence
- ORD record
- ord-3b917339f4624561921059be5fe813b9
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08623879B2
Reaction notes
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