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

HRID 2422522Notes

Reaction equation

HRID 2422522 reaction equation
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

Participants

6

Reactant 3

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

Product 1

HCID 113454577-Chloro-4-phenylquinoline

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-23fcca500ed046d58dd2d030b6f7b89b
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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