Pyridine, hydrofluoride (1:1) → 3-Fluoro-1,5-naphthyridine
Reaction equation
C1C=CN=CC=1.[FH:7].[N:8]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10](N)[CH:9]=1.N([O-])=O.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[F:7][C:10]1[CH:9]=[N:8][C:17]2[C:12]([CH:11]=1)=[N:13][CH:14]=[CH:15][CH:16]=2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To 2 mL of hydrogen fluoride/pyridine, 145 mg of 1,5-naphthyridin-3-amine was added at 0° C., 76 mg of sodium nitrite was added to the reaction mixture, and stirred at 0° C. for 1 hour. The reaction mixture was stirred at 60° C. for 1 hour, and neutralized with a saturated aqueous sodium hydrogen carbonate solution at 0° C., chloroform was then added thereto, and the organic layer was separated. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using silica gel; Silica Gel 60N made by KANTO CHEMICAL CO., INC., and an eluent of chloroform:methanol=20:1 to obtain 77 mg of 3-fluoro-1,5-naphthyridine as a light yellow solid.
Workup
- stirringThe reaction mixture was stirred at 60° C. for 1 hour
- customthe organic layer was separated
- washThe organic layer was washed with a saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe resultant residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-11a8691b39d643678ee2483cba125200
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367831B2
Reaction notes
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