Phosphorus oxychloride → 2-Chloro-6-fluoroquinoxaline

HRID 1852285

반응식

HRID 1852285 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[CH:6]=[N:5]2.[F:13][C:14]1[CH:23]=[C:22]2[C:17]([N:18]=[CH:19][C:20](=O)[NH:21]2)=[CH:16][CH:15]=1.O=P(Cl)(Cl)[Cl:27]>>[Cl:27][C:7]1[CH:6]=[N:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=1.[Cl:27][C:20]1[CH:19]=[N:18][C:17]2[C:22](=[CH:23][C:14]([F:13])=[CH:15][CH:16]=2)[N:21]=1

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 126863866-Fluoro-1,2-dihydroquinoxalin-2-oneHCID 217275347-fluoroquinoxalin-2(1H)-one

생성물 2

HCID 126864072-Chloro-6-fluoroquinoxaline수율 44%HCID 714639612-Chloro-7-fluoroquinoxaline수율 38%

실험 절차

A solution of 6-fluoroquinoxalin-2(1H)-one & 7-fluoroquinoxalin-2(1H)-one (3 g, 18.28 mmol) in POCl3 (20 ml) was refluxed for 3 h. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The aqueous solution was basified by solid sodium carbonate and extracted with ethyl acetate. The combine organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether) to afford regioisomers as a mixture. The above mixture was separated by SFC purification to afford 2-chloro-6-fluoroquinoxaline (0.75 g, 44%) and 2-chloro-7-fluoroquinoxaline (0.65 g, 38%) as white solid.

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with cold water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combine organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto get crude compound
  8. customThe crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether)
  9. customto afford regioisomers as a mixture
  10. customThe above mixture was separated by SFC purification

출처 및 근거

ORD 기록
ord-4126f29d182e41c5b04d03d581f02992
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957203B2

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