1,4-Dioxane → 2-Oxo-2H-pyrano[2,3-b]pyridine-7-carbaldehyde

HRID 657163Notes

Reaction equation

HRID 657163 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[O:8][C:9](=[O:12])[CH:10]=[CH:11][C:5]2=[CH:4][CH:3]=1.[O:13]1CCOCC1>C(Cl)Cl>[O:12]=[C:9]1[O:8][C:6]2=[N:7][C:2]([CH:1]=[O:13])=[CH:3][CH:4]=[C:5]2[CH:11]=[CH:10]1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 688173287-Methyl-2H-pyrano[2,3-b]pyridin-2-one

Product 1

HCID 866353742-Oxo-2H-pyrano[2,3-b]pyridine-7-carbaldehydeYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 7-methyl-2H-pyrano[2,3-b]pyridin-2-one (160 mg, 0.98 mmol) in 1,4-dioxane (12 mL) in a microwave reaction vial was added SeO2 (328 mg, 3.0 mmol). The reaction vial was capped and the mixture was heated in a microwave at 160° C. for 90 minutes. The reaction was diluted with DCM, filtered through a pad of Celite® and concentrated. The resulting material was dissolved in DCM and loaded onto a plug of silica gel and evaporated. Purification by column chromatography (silica gel) using a DCM/MeOH gradient (0-10% MeOH) provided the desired product as a pale yellow solid (120 mg, 40%). LCMS (ES+) m/z 176 (MH+).

Workup

  1. customThe reaction vial was capped
  2. filtrationfiltered through a pad of Celite®
  3. concentrationconcentrated
  4. dissolutionThe resulting material was dissolved in DCM
  5. customevaporated
  6. customPurification by column chromatography (silica gel)

Sources & evidence

ORD record
ord-94c6dffba7e94107999b15bc8837423a
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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