Sodium Carbonate → HCID 67528806, compound

HRID 1867547Notes

Reaction equation

HRID 1867547 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.[C:12](=[O:15])([O-])[O-].[Na+].[Na+]>C1(C)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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][OH:15])=[CH:8][CH:7]=2)=[CH:3][N:4]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 737434-Bromoisoquinoline

Product 1

HCID 67528806HCID 67528806, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, a mixture of 1.09 g (7.2 mmol) of (4-hydroxymethyl)phenylboronic acid, 1.24 g (6 mmol) of 4-bromoisoquinoline and 0.28 g (0.24 mmol) of palladium tetrakis(triphenylphosphine) in 50 ml of toluene and 10 ml of aqueous sodium carbonate solution (2M) is heated at reflux overnight. The filtrate is concentrated under reduced pressure and the residue is taken up in 150 ml of ethyl acetate and 40 ml of water. After the phases have settled and been separated, the organic phase is washed in succession with 20 ml of water and 20 ml of saturated aqueous sodium chloride solution. It is dried over sodium sulphate and the filtrate is concentrated under reduced pressure. The residue is purified by chromatography on silica gel, eluting with a 60/40 then 40/60 mixture of cyclohexane and ethyl acetate. This gives 1.12 g of a white solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. custombeen separated
  5. washthe organic phase is washed in succession with 20 ml of water and 20 ml of saturated aqueous sodium chloride solution
  6. dry with materialIt is dried over sodium sulphate
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe residue is purified by chromatography on silica gel
  9. washeluting with a 60/40
  10. addition40/60 mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-a1f7f31c04324003866d5c13c5e47645
Source dataset
uspto-grants-2009_12
Patent number
US07632850B2

Reaction notes

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