Selenium Dioxide → HCID 86674200, compound

HRID 241427Notes

Reaction equation

HRID 241427 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:5]([CH3:8])=[N:6][CH:7]=1.[Se](=O)=[O:15]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:5]([CH:8]=[O:15])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 15077476Ethyl 5-bromo-2-methylpyridine-3-carboxylate

Product 1

HCID 86674200HCID 86674200, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
180 °C

Procedure

To each of 106 separate 20-mL microwave vials, add: ethyl 5-bromo-2-methylpyridine-3-carboxylate (5 g, 20.48 mmol, 1.0 equiv), selenium dioxide (2.98 g, 26.63 mmol, 1.3 equiv), and 1,4-dioxane (13 mL). Heat the vessels to 180° C. for 20 min with microwave irradiation. Combine the contents of the reaction vessels; filter through a pad of silica gel (2 kg); and rinse the pad with DCM (3 L). Concentrate the combined filtrates under reduced pressure. Split the material into two equally-sized batches, and pass each through a pad of silica gel (2 kg) eluting with DCM. Concentrate the filtrate under reduced pressure to furnish the title compound as a yellow or pale orange solid (473 g, 93.2% yield). MS (m/z) (79Br/81Br) 258/260 (M+1).

Workup

  1. customTo each of 106 separate 20-mL microwave vials
  2. additionadd
  3. customwith microwave irradiation
  4. customthe contents of the reaction vessels
  5. filtrationfilter through a pad of silica gel (2 kg)
  6. washand rinse the pad with DCM (3 L)
  7. concentrationConcentrate the combined filtrates under reduced pressure
  8. customSplit the material into two equally-sized batches
  9. washeluting with DCM
  10. concentrationConcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-f942735894bd451296c273948a6f487e
Source dataset
uspto-grants-2014_02
Patent number
US08648200B2

Reaction notes

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