Cesium carbonate → 2-Fluoro-3-(pyridin-4-yl)pyridine
Reaction equation
Br[C:2]1[C:3]([F:8])=[N:4][CH:5]=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:8][C:3]1[C:2]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:7][CH:6]=[CH:5][N:4]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a 50 mL round-bottomed flask was added 3-bromo-2-fluoropyridine (1.0135 g, 5.759 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1.4577 g, 7.141 mmol), and trans-dichlorobis(triphenylphosphine)palladium(ii) (0.2138 g, 0.2879 mmol) in 1,2-dimethoxyethane. An aqueous solution of cesium carbonate (1.567 mL, 15.55 mmol) was added and the temperature was brought to 80° C. The reaction was monitored by LCMS to completion. The reaction mixture was diluted with water (10 mL) and extracted with DCM (3×10 mL). The organic extract was washed with water (1×10 mL), satd sodium chloride solution (1×10 mL), dried with magnesium sulfate, filtered, and concentrated. The solid was washed with ether and filtered to give 2-fluoro-3-(pyridin-4-yl)pyridine.
Workup
- customwas brought to 80° C
- extractionextracted with DCM (3×10 mL)
- extractionThe organic extract
- washwas washed with water (1×10 mL), satd sodium chloride solution (1×10 mL)
- dry with materialdried with magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- washThe solid was washed with ether
- filtrationfiltered
Sources & evidence
- ORD record
- ord-368685f6b4514970b8241cb0e0765eef
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637500B2
Reaction notes
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