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

HRID 2422522ノート

反応式

HRID 2422522 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 113454577-Chloro-4-phenylquinoline

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-23fcca500ed046d58dd2d030b6f7b89b
出典データセット
uspto-grants-2011_06
特許番号
US07960409B2

反応ノート

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