Potassium Carbonate → 3-Iodo-7-(2-methoxy-ethyl)-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione

HRID 1037229Notes

Reaction equation

HRID 1037229 reaction equation
[I:1][C:2]1[C:3](=[O:19])[C:4]2[CH:9]=[CH:8][NH:7][C:6](=[O:10])[C:5]=2[O:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:26][O:27][CH2:28][CH2:29]Br>CN(C=O)C>[I:1][C:2]1[C:3](=[O:19])[C:4]2[CH:9]=[CH:8][N:7]([CH2:29][CH2:28][O:27][CH3:26])[C:6](=[O:10])[C:5]=2[O:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 866710193-iodo-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione

Product 1

HCID 866710183-Iodo-7-(2-methoxy-ethyl)-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dioneYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-iodo-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione (100 mg, 0.27 mmol) in DMF (3 mL) was added potassium carbonate (55 mg, 0.40 mmol), followed by 2-bromoethyl methyl ether (28 μL, 0.37 mmol). The reaction mixture was stirred at RT for 24 hours. The resulting mixture was partitioned between ethyl acetate (40 mL) and water (20 mL) and the phases were separated. The organic layer was washed with brine (20 mL), dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was subjected to flash chromatography (SiO2, 60% ethyl acetate in cyclohexane) to give the title compound as a white solid (67 mg, 59%). LCMS (Method B): RT=3.94 min, [M+H]+=424.

Workup

  1. customThe resulting mixture was partitioned between ethyl acetate (40 mL) and water (20 mL)
  2. customthe phases were separated
  3. washThe organic layer was washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f38b2d779bbf4d94a243d1d5bf1ce704
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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