Selenium Dioxide → 3-Bromopyridine-2-carbaldehyde

HRID 747349Notes

Reaction equation

HRID 747349 reaction equation
[Br:1][C:2]1[C:3]([CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[Se](=O)=[O:10]>O1CCOCC1>[Br:1][C:2]1[C:3]([CH:8]=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 12010033-Bromo-2-methylpyridine

Product 1

HCID 164142313-Bromopyridine-2-carbaldehydeYield 29%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-bromo-2-picoline (prepared as described by Guthikonda, R. N.; Cama, L. D.; Quesada, M.; Woods, M. F.; Salzmann, T. N.; Christensen, B. G. J. Med. Chem. 1987, 30, 871-880) (249 mg, 1.45 mmol) in dioxane (2 mL) was added selenium(IV) oxide (212 mg, 1.91 mmol) and the mixture stirred at reflux overnight. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (Hexanes/ether, 3:1) to afford the title compound (78 mg, 29%) as a pale yellow solid. 1H NMR (CDCl3): δ 7.38 (dd, 1H, J=9, 6 Hz), 8.05 (d, 1H, J=9 Hz), 8.76 (d, 1H, J=3 Hz), 10.25 (s, 1H).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by column chromatography on silica gel (Hexanes/ether, 3:1)

Sources & evidence

ORD record
ord-4685b5e6a9ff41169cc12f4378cc5adc
Source dataset
uspto-grants-2008_07
Patent number
US07396840B2

Reaction notes

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