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

HRID 1772017ノート

反応式

HRID 1772017 の反応式
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]

参加物

4

反応物 2

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

生成物 1

HCID 866678085-Azido-1,6-naphthyridine収率 96%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-3ee252c0aa3f4f65bec25f4db2fe0225
出典データセット
uspto-grants-2016_02
特許番号
US09249162B2

反応ノート

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