Potassium Carbonate → 2-Cyclopropyl-4-(trifluoromethyl)pyridine
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.B([O-])([O-])O[CH:14]1[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(C)C=CC=CC=1>[CH:14]1([C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=2)[CH2:16][CH2:15]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To 21 ml of toluene were added 1.9 g of 2-chloro-4-trifluoromethylpyridine, 1 g of cyclopropyl borate, 2.92 g of potassium carbonate and 0.26 g of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane complex (1:1), and the mixture was stirred at 100° C. for 10 hours. After allowing to cool, the reaction solution was poured into an aqueous saturated ammonium chloride solution, and the resultant solution was extracted with diethyl ether three times, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 1 g of 2-cyclopropyl-4-trifluoromethylpyridine.
Workup
- temperatureto cool
- extractionthe resultant solution was extracted with diethyl ether three times
- washwashed with an aqueous saturated sodium chloride solution
- dry with materialdried with anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e4c54c416b7243aa8265405246bf6748
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318776B2
Reaction notes
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