Potassium Carbonate → HCID 66936637, compound

HRID 1943707Notes

Reaction equation

HRID 1943707 reaction equation
Br[C:2]1[CH:11]=[N:10][C:5]2[O:6][CH2:7][CH2:8][NH:9][C:4]=2[CH:3]=1.[O:12]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(#N)C>[O:12]1[CH:16]=[CH:15][C:14]([C:2]2[CH:11]=[N:10][C:5]3[O:6][CH2:7][CH2:8][NH:9][C:4]=3[CH:3]=2)=[CH:13]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2734358Furan-3-boronic acidHCID 667890617-bromo-1H,2H,3H-pyrido[2,3-b][1,4]oxazine

Product 1

HCID 66936637HCID 66936637, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 2.0 ml of acetonitrile/0.5 ml of distilled water, 7-bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (80 mg, 0.372 mmol), 3-furan boronic acid (45.7 mg, 0.409 mmol), palladium acetate (8.3 mg, 0.0372 mmol), triphenylphosphine (19.5 mg, 0.0744 mmol) and potassium carbonate (102.8 mg, 0.744 mmol) were added and reacted at 100□ for 10 min using microwave (50 W) apparatus. After completion of the reaction, the mixture was extracted with ethyl acetate, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by preparative TLC eluting a solvent of dichloromethane:methanol=20:1. Silica gels containing the product were eluted with dichloromethane and the solvent was evaporated to obtain 7-furan-3-yl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine in oil form (18 mg, 24%).

Workup

  1. customreacted at 100□ for 10 min
  2. customAfter completion of the reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by preparative TLC
  8. washeluting a solvent of dichloromethane
  9. additionSilica gels containing the product
  10. washwere eluted with dichloromethane
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8ab27137c7f7475f9c27aa0bf9012d5f
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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