Potassium Carbonate → HCID 66936594, compound

HRID 1943640Notes

Reaction equation

HRID 1943640 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.[CH:13]1(B(O)O)[CH2:15][CH2:14]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>[CH: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)[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2760897Cyclopropylboronic acidHCID 45901417-bromo-1H,2H,3H-pyrido[2,3-b][1,4]oxazin-2-one

Product 1

HCID 66936594HCID 66936594, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a 10 ml flask, 7-bromo-1H-pyrido[2,3-b][1,4]oxazin-2-one (400 mg, 1.746 mmol), cyclopropyl boronic acid (165 mg, 1.921 mmol), palladium acetate (39.1 mg, 0.174 mmol), triphenylphosphine (91.5 mg, 0.349 mmol) and potassium carbonate (482.6 mg, 3.492 mmol) were dissolved in a solvent of acetonitrile/water (6/1, 4.2 ml/0.9 ml). The reaction mixture was stirred for 60 minutes at 100□ using microwave (100 W) apparatus. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and the organic layer was washed with saturated saline solution. The combined organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of dichloromethane and ethyl acetate. The fractions containing the product were collected and evaporated to obtain a mixture (40 mg, 0.8%) containing triphenyl phosphoxide.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated saline solution
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica eluting with a solvent of dichloromethane and ethyl acetate
  7. additionThe fractions containing the product
  8. customwere collected
  9. customevaporated

Sources & evidence

ORD record
ord-41a6e9c425944aeea0b806cfad694d13
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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