Phosphorus oxychloride → 1-Chloro-4-(3-fluorophenyl)-6-methoxyisoquinoline-3-carbonitrile

HRID 639899노트

반응식

HRID 639899 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[NH:8][C:7]([C:14]#[N:15])=[C:6]2[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=1.O=P(Cl)(Cl)[Cl:25]>>[Cl:25][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:7]([C:14]#[N:15])[N:8]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 11995423HCID 11995423, 화합물

생성물 1

HCID 112438971-Chloro-4-(3-fluorophenyl)-6-methoxyisoquinoline-3-carbonitrile

실험 절차

42 mg of 6-methoxy-1-oxo-4-(3-fluorophenyl)-1,2-dihydroisoquinoline-3-carbonitrile in 3 mL POCl3 was heated from room temp to 80 C. After 2 h, the temperature was raised to 90 C, and heating was continued for 20 h. The reaction was concentrated, redissolved in EtOAc, cooled to 0 C, and saturated aqueous sodium bicarbonate was added dropwise to quench the remaining reagent. The mixture was separated, and the aqueous solution was extracted with EtOAc (3×). The combined organic solutions were dried over MgSO4 and concentrated. Flash chromatography (3% to 30% EtOAc in hexanes) gave a white solid.

후처리

  1. temperaturethe temperature was raised to 90 C
  2. temperatureheating
  3. waitwas continued for 20 h
  4. concentrationThe reaction was concentrated
  5. dissolutionredissolved in EtOAc
  6. temperaturecooled to 0 C, and saturated aqueous sodium bicarbonate
  7. additionwas added dropwise
  8. customto quench the remaining reagent
  9. customThe mixture was separated
  10. extractionthe aqueous solution was extracted with EtOAc (3×)
  11. dry with materialThe combined organic solutions were dried over MgSO4
  12. concentrationconcentrated
  13. customFlash chromatography (3% to 30% EtOAc in hexanes) gave a white solid

출처 및 근거

ORD 기록
ord-46ca07a5401f4d119a4445221cff40fa
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691879B2

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