Pyridine, hydrofluoride (1:1) → 3-Fluoro-1,5-naphthyridine

HRID 385613ノート

反応式

HRID 385613 の反応式
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]=2

参加物

6

反応物 4

HCID 64774Pyridine, hydrofluoride (1:1)HCID 516892Sodium BicarbonateHCID 5893511,5-Naphthyridin-3-amineHCID 23668193Sodium Nitrite

生成物 1

HCID 534161913-Fluoro-1,5-naphthyridine

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  1. stirringThe reaction mixture was stirred at 60° C. for 1 hour
  2. customthe organic layer was separated
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-11a8691b39d643678ee2483cba125200
出典データセット
uspto-grants-2013_02
特許番号
US08367831B2

反応ノート

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