Potassium Hydroxide → HCID 18979075, compound

HRID 2393089Notes

Reaction equation

HRID 2393089 reaction equation
[OH-].[K+].Br[C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[CH:9][CH:10]=2)[N:5]=1.C(B(CC)[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[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>[CH3:15][O:14][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[CH:13]=[CH:12]2

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 6428513-(Diethylboryl)pyridineHCID 155274252-Bromo-8-methoxyquinoline

Product 1

HCID 18979075HCID 18979075, compoundYield 82.3%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Powdered potassium hydroxide (675 mg) was added to a stirred mixture of 2-bromo-8-methoxyquinoline (956 mg), diethyl(3-pyridyl)borane (590 mg), tetrakis(triphenylphosphine)-palladium(0) (250 mg) and tetra-n-butylammonium iodide (740 mg) in anhydrous tetrahydrofuran (60ml). The stirred mixture was refluxed under an inert atmosphere for 1.25 h. The solvent was removed in vacuo and the residue partitioned between dichloromethane (100 ml) and water (80ml). The aqueous phase was reextracted with dichloromethane (2×50 ml) and the combined organic phases were dried (magnesium sulfate), filtered through a small pad of Celite and evaporated in vacuo. The crude product was purified by flash chromatography on silica, eluting with ethyl acetate to yield the title compound (780 mg) as a clear oil.

Workup

  1. temperatureThe stirred mixture was refluxed under an inert atmosphere for 1.25 h
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between dichloromethane (100 ml) and water (80ml)
  4. dry with materialthe combined organic phases were dried (magnesium sulfate)
  5. filtrationfiltered through a small pad of Celite
  6. customevaporated in vacuo
  7. customThe crude product was purified by flash chromatography on silica
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-fa4affadd0b94bbbbf9c11d41f24967d
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

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