Sodium Carbonate → 3-(3-Quinolinyl)benzenamine

HRID 240103Notes

Reaction equation

HRID 240103 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3](B(O)O)[CH:2]=1.Br[C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:15]2[CH:16]=[C:17]([NH2:18])[CH:19]=[CH:20][CH:21]=2)[CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115623-BromoanilineHCID 2734663Quinoline-3-boronic acid

Product 1

HCID 41343023-(3-Quinolinyl)benzenamineYield 53%

Reagents, catalysts & solvents 2

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

Procedure

Quinoline-3-boronic acid (0.120 g, 0.693 mmol) and 3-bromoaniline (0.05 mL, 0.462 mmol) were combined in dimethoxyethane (DME, 2 mL) in a flame-dried, round-bottom flask. Sodium carbonate (Na2CO3, 2M, 0.485 mL, 0.970 mmol) and tetrakis[triphenylphosphine]palladium(0) (Pd(PPh3)4, 0.017 g, 0.014 mmol) were added to the stirred solution. The reaction was refluxed overnight under argon flow, and subsequently cooled to room temperature. The solvent was removed under vacuum, and the residue was resuspended in H20 and extracted with methylene chloride (CH2Cl2). The organic phase was dried over magnesium sulfate (MgSO4) and concentrated under vacuum. The crude product was purified by silica column chromatography (0-5% methanol (MeOH)/CH2Cl2). The purification was monitored by thin layer chromatography (TLC). The solvent was removed under vacuum from fractions containing product, resulting in 0.054 g in 53% yield.

Workup

  1. temperatureThe reaction was refluxed overnight under argon flow
  2. customThe solvent was removed under vacuum
  3. extractionextracted with methylene chloride (CH2Cl2)
  4. dry with materialThe organic phase was dried over magnesium sulfate (MgSO4)
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by silica column chromatography (0-5% methanol (MeOH)/CH2Cl2)
  7. customThe purification
  8. customThe solvent was removed under vacuum from fractions
  9. additioncontaining product
  10. customresulting in 0.054 g in 53% yield

Sources & evidence

ORD record
ord-c1ebbd13cfb341d9b75a03323487e345
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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