Sodium Azide → 5-Azido-1,6-naphthyridine

HRID 1615651노트

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HRID 1615651 반응식
Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C=O)C>[N:12]([C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2)=[N+:13]=[N-:14]

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 122042345-Chloro-1,6-naphthyridine

생성물 1

HCID 866678085-Azido-1,6-naphthyridine수율 96%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

A solution of 5-chloro-1,6-naphthyridine (500 mg, 3.04 mmol) in DMF (5 mL) was stirred at room temperature. Sodium azide (592 mg, 9.12 mmol) was added to the mixture, and the mixture was stirred at 80° C. for 4 h. The mixture was cooled to room temperature and filtered through Celite to remove a white solid. The filtrate was diluted with EtOAc (25 mL) and washed with brine (5×5 mL). The combined organic layers were dried with Na2SO4, filtered, and the solvent was removed under reduced pressure to yield 5-azido-1,6-naphthyridine as a yellow solid, which was used in the next step without further purification (500 mg, yield 96%). ESI MS: m/z 172 [M+H]+.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. customto remove a white solid
  4. additionThe filtrate was diluted with EtOAc (25 mL)
  5. washwashed with brine (5×5 mL)
  6. dry with materialThe combined organic layers were dried with Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-7fd36aaf3ae043b083618cd9d1574684
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765760B2

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