Pyridine → HCID 117665492, compound

HRID 1771083Notes

Reaction equation

HRID 1771083 reaction equation
[CH3:1][O:2][S:3]([C:6]([F:9])([F:8])[F:7])(=[O:5])=[O:4].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([CH:18]=[O:19])[CH:13]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[OH:5][S:3]([C:6]([F:9])([F:8])[F:7])(=[O:4])=[O:2].[CH3:1][N:15]1[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]1[CH:18]=[O:19]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 9526Methyl triflate2×HCID 123253904-Methoxypyridine-2-carboxaldehyde

Product 1

HCID 117665492HCID 117665492, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 3 mL glass vial was equipped with a rubber septum and magnetic stir bar. The vial was brought into a glove box and charged with MeOTf (116 μL, 1.06 mmol) by micropipette. The vial was sealed and removed from the glove box. A separate 3 mL vial was charged with 4-methoxy-2-pyridinecarboxaldehyde (Astatech C10253, 145 mg, 106 mmol) and was dissolved in PhMe (1 mL). The solution of pyridine was added via syringe onto the MeOTf at room temperature. The vial which contained the pyridine was rinsed with PhMe (0.5 mL) and the rinse solution was injected into the reaction vial. The reaction vial was kept at room temperature and stirring was maintained at ca. 400-600 rpm. After 20 h, hexanes (2 mL) were added after which stirring was stopped. Any solid or oil was allowed to settle and the solvent was removed by glass pipette. The solid or oil was then rinsed with several portions of hexanes followed by diethyl ether. Residual solvent was then removed in vacuo to provide the compound N-methyl-4-methoxy-2-pyridinecarboxaldehyde triflate (300 mg, 94%). This oil was used for oxime formation without further purification.

Workup

  1. customThe vial was brought into a glove box
  2. customThe vial was sealed
  3. customremoved from the glove box
  4. washwas rinsed with PhMe (0.5 mL)
  5. customThe reaction
  6. customvial was kept at room temperature
  7. temperaturewas maintained at ca. 400-600 rpm
  8. stirringstirring
  9. customthe solvent was removed by glass pipette
  10. washThe solid or oil was then rinsed with several portions of hexanes
  11. customResidual solvent was then removed in vacuo

Sources & evidence

ORD record
ord-0f0afbb1561944b596048cf44014bc57
Source dataset
uspto-grants-2016_02
Patent number
US09249100B2

Reaction notes

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