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

HRID 385613노트

반응식

HRID 385613 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 534161913-Fluoro-1,5-naphthyridine

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-11a8691b39d643678ee2483cba125200
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367831B2

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