4,7-Dichloroquinoline → 7-Chloro-4-phenylquinoline

HRID 2422522노트

반응식

HRID 2422522 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[F-].[Cs+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

참가 물질

6

반응물 3

HCID 68664,7-DichloroquinolineHCID 25953Cesium fluorideHCID 66827Phenylboronic Acid

생성물 1

HCID 113454577-Chloro-4-phenylquinoline

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of 4,7-dichloroquinoline (12.5 g, 63.1 mmol), phenylboronic acid (9.63 g, 79 mmol) and cesium fluoride (24 g, 158 mmol) in 1,2-dimethoxyethane (300 mL) was degassed and purged three times with nitrogen gas before the addition of the tetrakis(triphenylphosphine) palladium(0) (3.64 g, 3.15 mmol). The resultant mixture was then stirred at reflux overnight. After cooling, the reaction was filtered over celite and washed with dichloromethane. After evaporation under reduced pressure, the residue was purified by column chromatography (eluting with hexane/EtOAc, 95:5) to yield the title compound. 1H NMR (400 MHz, acetone-d6): δ 9.0 (d, 1H), 8.15 (d, 1H), 7.95 (d, 1H), 7.65-7.55 (m, 6H), 7.5 (d, 1H).

후처리

  1. customwas degassed
  2. custompurged three times with nitrogen gas
  3. temperatureat reflux overnight
  4. temperatureAfter cooling
  5. filtrationthe reaction was filtered over celite
  6. washwashed with dichloromethane
  7. customAfter evaporation under reduced pressure
  8. customthe residue was purified by column chromatography (eluting with hexane/EtOAc, 95:5)

출처 및 근거

ORD 기록
ord-23fcca500ed046d58dd2d030b6f7b89b
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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