Phosphorus oxychloride → 3-(4-(1H-Pyrazol-1-yl)benzyl)-6-bromo-2,4-dichloro-8-fluoroquinoline

HRID 928783

반응식

HRID 928783 반응식
[N:1]1([C:6]2[CH:27]=[CH:26][C:9]([CH2:10][C:11]3[C:12](OC)=NC4C([C:20]=3[Cl:21])=CC(Br)=CC=4C)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[Br:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[C:31]([F:36])[CH:30]=1.O=P(Cl)(Cl)[Cl:39]>>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][C:11]3[C:20]([Cl:21])=[N:33][C:32]4[C:34]([C:12]=3[Cl:39])=[CH:35][C:29]([Br:28])=[CH:30][C:31]=4[F:36])=[CH:26][CH:27]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

참가 물질

4

반응물 3

HCID 24813Phosphorus oxychlorideHCID 1230504-Bromo-2-fluoroanilineHCID 867155993-(4-(1H-Pyrazol-1-yl)benzyl)-6-bromo-4-chloro-2-methoxy-8-methylquinoline2회

생성물 1

HCID 867156193-(4-(1H-Pyrazol-1-yl)benzyl)-6-bromo-2,4-dichloro-8-fluoroquinoline

반응 조건

온도
105 °C

실험 절차

A mixture of 2-(4-(1H-pyrazol-1-yl)benzyl)malonic acid (4 g, 15.37 mmol, Intermediate 6: step b) and 4-bromo-2-fluoroaniline (2.7 g, 13.973 mmol) in POCl3 (20 mL) was heated at 105° C. for 3 hours, cooled to room temperature and evaporated in vacuo to remove excess POCl3. The residue was poured into ice H2O and treated with aqueous NH4OH to pH 8-9 (temperature of the aqueous mixture was kept cold during addition). The precipitates were collected, rinsed with H2O and dried under reduced pressure. The solids were diluted with DCM and insoluble solids filtered off. The filtrate was evaporated to dryness to provide product as a tan solid.

후처리

  1. temperaturecooled to room temperature
  2. customevaporated in vacuo
  3. customto remove excess POCl3
  4. additionThe residue was poured into ice H2O
  5. additiontreated with aqueous NH4OH to pH 8-9 (temperature of the aqueous mixture
  6. additionwas kept cold during addition)
  7. customThe precipitates were collected
  8. washrinsed with H2O
  9. customdried under reduced pressure
  10. additionThe solids were diluted with DCM and insoluble solids
  11. filtrationfiltered off
  12. customThe filtrate was evaporated to dryness
  13. customto provide product as a tan solid

출처 및 근거

ORD 기록
ord-c2f704ef51e84d1c978674d2b298a349
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290476B2

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