Potassium Carbonate → 7-Phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

HRID 1943650Notes

Reaction equation

HRID 1943650 reaction equation
Br[C:2]1[CH:12]=[N:11][C:5]2[O:6][CH2:7][C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:13]1([C:2]2[CH:12]=[N:11][C:5]3[O:6][CH2:7][C:8](=[O:10])[NH:9][C:4]=3[CH:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 45901417-bromo-1H,2H,3H-pyrido[2,3-b][1,4]oxazin-2-one

Product 1

HCID 669367437-Phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-oneYield 44.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a 10 ml flask equipped with refluxing apparatus, 7-bromo-1H-pyrido[2,3-b][1,4]oxazin-2-one (48 mg, 0.21 mmol), phenyl boronic acid (PhB(OH)2, 28 mg, 0.23 mmol), triphenylphosphine (PPh3, 11 mg, 0.04 mmol), palladium acetate (Pd(OAc)2, 5 mg, 0.02 mmol), potassium carbonate (44 mg, 0.31 mmol) were dissolved in acetonitrile (1.6 ml) and water (0.4 ml). The mixture was heated to 90□ and then refluxed for 15 hours. The mixture was evaporated and water was added, and then the mixture was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica eluting with a solvent of dichloromethane:methanol=30:1. The fractions containing the product were collected and evaporated to obtain pale-brown solid (21 mg, 44%).

Workup

  1. customTo a 10 ml flask equipped
  2. temperatureThe mixture was heated to 90□
  3. temperaturerefluxed for 15 hours
  4. customThe mixture was evaporated
  5. additionwater was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe resulting residue was purified by column chromatography on silica eluting with a solvent of dichloromethane
  11. additionThe fractions containing the product
  12. customwere collected
  13. customevaporated

Sources & evidence

ORD record
ord-283eb0ec9a184242a8b80cb4650edce5
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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